Anilide derivatives and their use for combating botrytis

ABSTRACT

The use of nicotinic anilide derivatives of the general formula ##STR1## where the substituents have the following meanings: R 1  halogen, methyl, trifluoromethyl, methoxy, methylthio, methylsulfinyl, methylsulfonyl 
     R 2  unsubstituted or halogen-substituted alkyl, unsubstituted or halogen-substituted alkenyl, alkynyl, unsubstituted or halogen-substituted alkoxy, unsubstituted or halogen-substituted alkenyloxy, alkynyloxy, cycloalkyl, cycloalkenyl, cycloalkyloxy, cycloalkenyloxy 
     for combating Botrytis, and nicotinic anilides of the formula I.

This is a Division of application Ser. No. 08/215,463, filed on Mar. 21, 1994, U.S. Pat. No. 5,480,897, which is a divisional application of Ser. No. 07/973,976, filed on Nov. 9, 1992, U.S. Pat. No. 5,330,995.

The present invention relates to the use of anilide derivatives of the general formula ##STR2## where A has the following meanings: pyridin-3-yl substituted in the 2-position by halogen, methyl, trifluoromethyl, methoxy, methylthio, methylsulfinyl or methylsulfonyl,

phenyl substituted in 2-position by methyl, trifluoromethyl, chlorine, bromine or iodine,

2-methyl-5,6-dihydropyran-3-yl, 2-methyl-5,6-dihydro-1,4-oxathiin-3-yl,2-methyl-5,6-dihydro-1,4-oxathiin-3-yl-4-oxide, 2-methyl-5,6-dihydro-1,4-oxathiin-3-yl-4,4-dioxide; 2-methyl-furan-3-yl substituted in the 4- and 5-positions by hydrogen or methyl; thiazol-5-yl substituted in the 2- and 4-positions by hydrogen, methyl, chlorine or trifluoromethyl; thiazol-4-yl substituted in the 2- and 5-positions by hydrogen, methyl, chlorine or trifluoromethyl; 1-methylpyrazol-4-yl substituted in the 3- and 5-positions by methyl, chlorine or trifluoromethyl; or oxazol-5-yl substituted the 2- and 4-positions by hydrogen, methyl or chlorine, and

R has the following meanings: unsubstituted or halogen-substituted C₂ -C₁₂ -alkyl, unsubstituted or halogen-substituted C₃ -C₁₂ -alkenyl, C₃ -C₆ -alkynyl, unsubstituted or halogen-substituted C₂ -C₁₂ -alkoxy, unsubstituted or halogen-substituted C₃ -C₁₂ -alkenyloxy, C₃ -C₁₂ -alkynyloxy, unsubstituted or C₁ -C₄ -alkyl-substituted C₃ -C₆ -cycloalkyl, unsubstituted or C₁ -C₄ -alkyl-substituted C₄ -C₆ -cycloalkenyl, unsubstituted or C₁ -C₄ -alkyl-substituted C₅ -C₆ -cycloalkyloxy, unsubstituted or C₁ -C₄ -alkyl-substituted C₅ -C₆ -cycloalkenyloxy, or phenyl which is unsubstituted or substituted by C₁ -C₁₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio or halogen,

for combating Botrytis.

The present invention further relates to novel anilide derivatives.

It is known to use nicotinic anilides, e.g., 2-chloronicotic-2'-ethylanilide (U.S. Pat. No. 4,001,416) and 2-chloronicotic-3'-isopropyl-anilide (DE 26 11 601), as fungicides.

We have now found that the anilide derivatives defined at the outset have a good action on Botrytis.

In view of their action, those compounds are preferred in which the substituents have the following meanings:

halogen, e.g., fluorine, chlorine and bromine,

alkyl, especially ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,2-dimethylpropyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,3-dimethylbutyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 3,3-dimethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethylbutyl, 2-ethylbutyl, 1-ethyl-2-methylpropyl, n-heptyl, 1-methylhexyl, 1-ethylpentyl, 2-ethylpentyl, 1-propylbutyl, octyl, decyl or dodecyl, where alkyl may bear from one to three of the abovementioned halogen atoms, especially fluorine and chlorine,

alkenyl, such as 2-propenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-2-propenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 1-ethyl-2-butenyl, 1-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl and 1-ethyl-2-methyl-2-propenyl, especially 2-propenyl, 2-butenyl, 3-methyl-2-butenyl and 3-methyl-2-pentenyl, where alkenyl may bear from one to three of the abovementioned halogen atoms, especially fluorine and chlorine,

alkynyl, such as 2-propynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 1-methyl-2-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 2-hexynyl, 3-hexynyl, 4-alkynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-4-pentynyl, 4-methyl-2-pentynyl, 1,2-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl,

alkoxy, especially ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy, n-pentyloxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,2-dimethylpropoxy, 1,1-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, n-hexyloxy, 1-methylpentyloxy, 2-methylpentyloxy, 3-methylpentyloxy, 4-methylpentyloxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,3-dimethylbutoxy, 1,1-dimethylbutoxy, 2,2-dimethylbutoxy, 3,3-dimethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1-ethyl-2-methylpropoxy, n-heptyloxy, 1-methylhexyloxy, 2-methylhexyloxy, 3-methylhexyloxy, 4-methylhexyloxy, 5-methylhexyloxy, 1-ethylpentyloxy, 2-ethylpentyloxy, 1-propylbutoxy, octyloxy, decyloxy, and dodecyloxy, where alkoxy may bear from one to three of the abovementioned halogen atoms, especially fluorine and chlorine,

alkenyloxy such as 2-propenyloxy, 2-butenyloxy, 3-butenyloxy, 1-methyl-2-propenyloxy, 2-methyl-2-propenyloxy, 2-pentenyloxy, 3-pentenyloxy, 4-pentenyloxy, 1-methyl-2-butenyloxy, 2-methyl-2-butenyloxy, 3-methyl-2-butenyloxy, 1-methyl-3-butenyloxy, 2-methyl-3-butenyloxy, 3-methyl-3-butenyloxy, 1,1-dimethyl-2-propenyloxy, 1,2-dimethyl-2-propenyloxy, 1-ethyl-2-propenyloxy, 2-hexenyloxy, 3-hexenyloxy, 4-hexenyloxy, 5-hexenyloxy, 1-methyl-2-pentenyloxy, 2-methyl-2-pentenyloxy, 3-methyl-2-pentenyloxy, 4-methyl-2-pentenyloxy, 1-methyl-3-pentenyloxy, 2-methyl-3-pentenyloxy, 3-methyl-3-pentenyloxy, 4-methyl-3-pentenyloxy, 1-methyl-4-pentenyloxy, 2-methyl-4-pentenyloxy, 3-methyl-4-pentenyloxy, 4-methyl-4-pentenyloxy, 1,1-dimethyl-2-butenyloxy, 1,1-dimethyl-3-butenyloxy, 1,2-dimethyl-2-butenyloxy, 1,2-dimethyl-3-butenyloxy, 1,3-dimethyl-2-butenyloxy, 1,3-dimethyl-3-butenyloxy, 2,2-dimethyl-3-butenyloxy, 2,3-dimethyl-2-butenyloxy, 2,3-dimethyl-3-butenyloxy, 1-ethyl-2-butenyloxy, 1-ethyl-3-butenyloxy, 2-ethyl-2-butenyloxy, 2-ethyl-3-butenyloxy, 1,1,2-trimethyl-2-propenyloxy, 1-ethyl-1-methyl-2-propenyloxy and 1-ethyl-2-methyl-2-propenyloxy, especially 2-propenyloxy, 2-butenyloxy, 3-methyl-2-butenyloxy and 3-methyl-2-pentenyloxy;

where alkenyloxy may bear from one to three of the abovementioned halogen atoms, especially fluorine and chlorine;

alkynyloxy such as 2-propynyloxy, 2-butynyloxy, 3-butynyloxy, 1-methyl-2-propynyloxy, 2-pentynyloxy, 3-pentynyloxy, 4-pentynyloxy, 1-methyl-3-butynyloxy, 2-methyl-3-butynyloxy, 1-methyl-2-butynyloxy, 1,1-dimethyl-2-propynyloxy, 1-ethyl-2-propynyloxy, 2-hexynyloxy, 3-hexynyloxy, 4-alkynyloxy, 5-hexynyloxy, 1-methyl-2-pentynyloxy, 1-methyl-3-pentynyloxy, 1-methyl-4-pentynyloxy, 2-methyl-3-pentynyloxy, 2-methyl-4-pentynyloxy, 3-methyl-4-pentynyloxy, 4-methyl-3-pentynyloxy, 1,1-dimethyl-2-butynyloxy, 1,1-dimethyl-3-butynyloxy, 1,2-dimethyl-3-butynyloxy, 2,2-dimethyl-3-butynyloxy, 1-ethyl-2-butynyloxy, 1-ethyl-3-butynyloxy, 2-ethyl-3-butynyloxy and 1-ethyl-1-methyl-2-propynyloxy, preferably 2-propynyloxy, 2-butynyloxy, 1-methyl-2-propynyloxy and 1-methyl-2-butynyloxy,

C₃ -C₆ -cyanoalkyl, such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl, where cycloalkyl is unsubstituted or substituted by one to three C₁ -C₄ -alkyl radicals;

C₄ -C₆ -cyanoalkenyl, such as cyclobutenyl, cyclopentenyl and cyclohexenyl, which is unsubstituted or substituted by one to three C₁ -C₄ -alkyl radicals;

C₅ -C₆ -cycloalkoxy such as cyclopentyloxy or cyclohexyloxy, which may be substituted by one to three C₁ -C₄ -alkyl radicals;

C₅ -C₆ -cycloalkenyloxy such as cyclopentyloxy or cyclohexaryloxy, which may be substituted by one to three C₁ -C₄ -alkyl radicals.

For combating Botrytis, the use of nicotinic anilide derivatives of the formula I in which the substituents have the meanings given below is preferred: ##STR3## R¹ halogen, methyl, trifluoromethyl, methoxy, methylthio, methylsulfinyl, methylsulfonyl

R² unsubstituted or halogen-substituted C₂ -C₁₂ -alkyl, unsubstituted or halogen-substituted C₃ -C₁₂ -alkenyl, C₃ -C₆ -alkynyl, unsubstituted or halogen-substituted C₂ -C₁₂ -alkoxy, unsubstituted or halogen-substituted C₃ -C₁₂ -alkenyloxy, C₃ -C₁₂ -alkynyloxy, C₃ -C₆ -cycloalkyl, C₄ -C₆ -cycloalkenyl, C₅ -C₆ -cycloalkyloxy, C₅ -C₆ -cycloalkenyloxy.

The compounds of the formula I are obtained for instance by reacting a correspondingly substituted nicotinic halide of the formula 2 ##STR4## Hal denoting chlorine or bromine, with an ortho-substituted aniline of the formula 3 in the presence of a base. The nicotinic acids and their halides of the formula 2 are known. The anilines of the formula 3 are known or can be prepared by known methods (Helv. Chim. Acta 60, 978 (1977); Zh. Org. Khim 26, 1527(1990); Heterocyclus 26, 1885 (1987); Izv. Akad. Nauk. SSSR Ser.Khim 1982, 2160).

Compounds of the formula I in which R¹ is chlorine and R² has the meanings given above are particularly preferred.

                  TABLE 1     ______________________________________     Compounds of the formula I      ##STR5##                      I                                   Phys. data     No.  R1       R2              m.p. [°C.]     ______________________________________     1.1  F        n-C.sub.3 H.sub.7     1.2  F        i-C.sub.3 H.sub.7     1.3  F        sec.-C.sub.4 H.sub.9                                   52-54     1.4  F        i-C.sub.4 H.sub.9                                   87-89     1.5  Cl       n-C.sub.3 H.sub.7                                   103-104     1.6  Cl       n-C.sub.4 H.sub.9     1.7  Cl       sec.-C.sub.4 H.sub.9                                   94-96     1.8  Cl       i-C.sub.4 H.sub.9                                    99-101     1.9  Cl       tert.-C.sub.4 H.sub.9                                   118-120     1.10 Cl       n-C.sub.5 H.sub.11     1.11 Cl       sec.-C.sub.5 H.sub.11     1.12 Cl       n-C.sub.6 H.sub.13     1.13 Cl       n-C.sub.7 H.sub.15     1.14 Cl       sec.-C.sub.7 H.sub.15     1.15 Cl       n-C.sub.8 H.sub.17     1.16 Cl       n-C.sub.10 H.sub.23     1.17 Cl       n-C.sub.12 H.sub.25     1.18 Cl       1-Methylvinyl   90-91     1.19 Cl       2-Methylvinyl     1.20 Cl       Allyl     1.21 Cl       2-Methylallyl     1.22 Cl       2-Ethylallyl     1.23 Cl       1-Methylallyl     1.24 Cl       1-Ethylallyl     1.25 Cl       1-Methyl-2-butenyl     1.26 Cl       1-Ethyl-2-butenyl     1.27 Cl       1-Isopropyl-2-butenyl     1.28 Cl       1-n-Butyl-2-butenyl     1.29 Cl       1-Methyl-2-pentenyl     1.30 Cl       1,4-Dimethyl-2-pentenyl     1.31 Cl       Propargyl     1.32 Cl       2-Butynyl     1.33 Cl       3-Butynyl     1.34 Cl       Ethoxy          131-132     1.35 Cl       Propoxy     1.36 Cl       1-Methylethoxy  65-67     1.37 Cl       n-Butoxy        84-85     1.38 Cl       1-Methylpropoxy 72-74     1.39 Cl       2-Methylpropoxy 81-84     1.40 Cl       1,1-Dimethylethoxy     1.41 Cl       n-Pentyloxy     1.42 Cl       n-Hexyloxy     1.43 Cl       n-Hepyloxy     1.44 Cl       n-Octyloxy     1.45 Cl       2-Ethylhexyloxy     1.46 Cl       n-Decyloxy     1.47 Cl       2-Propenyloxy   86-88     1.48 Cl       2-Butenyloxy    92-95     1.49 Cl       2-Methyl-2-propenyloxy                                   75-76     1.50 Cl       2-Pentenyloxy     1.51 Cl       3-Pentenyloxy     1.52 Cl       3-chloro-2-propenyloxy     1.53 Cl       2,3-Dichloro-2-                   propenyloxy     1.54 Cl       2,3,3-Trichloro-propenyl                   oxy     1.55 Cl       2-Propynyloxy   79-84     1.56 Cl       2-Butynyl-oxy     1.57 Cl       3-Butynyl-oxy     1.58 Cl       1-Methyl-2-propynyloxy     1.59 Cl       Cyclopropyl     144-145     1.60 Cl       Cyclobutyl     1.61 Cl       Cyclopentyl     112-114     1.62 Cl       Cyclohexyl      141-142     1.63 Cl       2-Cyclopentenyl 123-124     1.64 Cl       1-Cyclopentenyl     1.65 Cl       2-Cyclohexenyl  92-93     1.66 Cl       1-Cyclohexenyl     1.67 Cl       Cyclopentyloxy  80-82     1.68 Cl       Cyclohexyloxy     1.69 Cl       2-Cyclopentenyloxy     1.70 Cl       2-Cyclohexenyloxy                                   oil     1.71 Br       sec.-Butyl     1.72 Br       i-Butyl     1.73 CH.sub.3 sec.-Butyl     1.74 CH.sub.3 i-Butyl     1.75 CF.sub.3 i-Propyl     1.76 CF.sub.3 sec.-Butyl     1.77 CF.sub.3 i-Butyl     1.78 OCH.sub.3                   i-Propyl     1.79 OCH.sub.3                   sec.-Butyl      oil NMR 0.8t(3H);                                   1.2d(3H); 1.6m(2H);                                   3.0q(1H); 4.1s(3H);                                   7.2m(3H); 7.3m(1H);                                   8.3m(1H); 8.4m(1H),                                   9.8s(1H)     1.80 OCH.sub.3                   i-Butyl         oil NMR 0,8d(6H);                                   1.9m(1H); 2.5d(2H),                                   4.05s(3H), 7.2m(4H);                                   7.8d(1H); 8.3d(1H);                                   8.4m(1H); 9.8s(1H)     1.81 SCH.sub.3                   i-Propyl     1.82 SCH.sub.3                   sec.-Butyl      89-91     1.83 SCH.sub.3                   i-Butyl         140-141     1.84 SO.sub.2 CH.sub.3                   sec.-Butyl      191-192     1.85 SO.sub.2 CH.sub.3                   i-Butyl         150-153     1.86 Cl       2-Ethylpropoxy  65-66     1.87 Cl       3-Methyl-3-butenyloxy                                   83-84     ______________________________________

MANUFACTURING EXAMPLES Example 1

At 0° C., 3.5 g of 2-chloroonicotic chloride is dripped into a solution of 2.7 g of 2-n-propylaniline and 2.0 g of triethylamine in 30 ml of tetrahydrofuran, and the mixture is stirred for 2 hours at 0° C. After dilution with 300 ml of water, there is isolated 3.2 g of 2-chloronicotic acid-2-n-propylanilide; m.p.: 103°-104° C. (No. 1.5).

Example 2

4.4 g of 2-chloroonicotic acid-2-sec.-butylanilide (Table 1, No. 7) is refluxed for 2 hours in a solution of 5.5 g of 30% strength sodium methylate solution in 20 ml of methanol. After dilution with 250 ml of water the mixture is extracted twice, each time with 100 ml of ethyl acetate. From the combined organic phases there is isolated, after drying and evaporation of the solvent, 3.8 g of 2-methoxy-nicotinic acid-2-sec.-butylanilide as an oil (No. 1.79).

Example 3

Similarly to Example 1, there is obtained from 5.7 g of 2-methylthionicotic chloroide, 4.6 g of 2-sec-butylaniline and 3.1 g of triethylamine 6.6 g of 2-methylthionicotic acid-2-sec.-butylanilide; m.p.: 89°-91° C. (No. 1.82).

Example 4

While stirring at 35° C., 2.20 g of 30% strength hydrogen peroxyde is dripped into a mixture of 2.00 g of the abovementioned product (Example 3) in 5 ml of glacial acetic acid and 0.13 g of sodium tungstate, and the mixture is stirred for 3 hours at 35° C. After dilution with 15 ml of water, removal of the crystals by suction filtration, washing with water and drying, there is obtained 1.7 g of 2-methylsulfonylnicotic acid-2-sec.-butylanilide; m.p.: 191°-192° C. (No. 1.84).

The invention further relates to the use of anilide derivatives of the formula II ##STR6## where the substituents have the following meanings: ##STR7## X methylene or sulfur R unsubstituted or halogen-substituted C₃ -C₁₂ -alkyl, unsubstituted or halogen-substituted C₃ -C₁₂ -alkenyl, C₃ -C₆ -alkynyl, unsubstituted or halogen-substituted C₂ -C₁₂ -alkoxy, unsubstituted or halogen-substituted C₃ -C₁₂ -alkenyloxy, C₃ -C₁₂ -alkynyloxy, unsubstituted or C₁ -C₄ -alkyl-substituted C₃ -C₆ -cycloalkyl, unsubstituted or C₁ -C₄ -alkyl-substituted C₄ -C₆ -cycloalkenyl, unsubstituted or C₁ -C₄ -alkyl-substituted C₅ -C₆ -cycloalkyloxy, unsubstituted or C₁ -C₄ -alkyl-substituted C₅ -C₆ -cycloalkenyloxy

for combating Botrytis.

The compounds of the formula 2 are obtained for instance by reacting a correspondingly substituted carboxylic halide of the formula 4 with an ortho-substituted aniline of the formula 3 in the presence of a base: ##STR8## Hal is chlorine or bromine.

The carboxylic acids and their halides ACO₂ H and A--CO--Hal (4) are known.

                  TABLE 2     ______________________________________     Compounds of the formula II      ##STR9##                                         Phys. data     No.   A     R                  X    mp [°C.]     ______________________________________     2.1   A.sub.1                 i-C.sub.3 H.sub.7  --   108-109     2.2   A.sub.1                 n-C.sub.3 H.sub.7  --   112-114     2.3   A.sub.1                 n-C.sub.4 H.sub.9  --     2.4   A.sub.1                 sec.-C.sub.4 H.sub.9                                    --   89-90     2.5   A.sub.1                 i-C.sub.4 H.sub.9  --   118-11     2.6   A.sub.1                 tert.-C.sub.4 H.sub.9                                    --     2.7   A.sub.1                 n-C.sub.5 H.sub.11 --     2.8   A.sub.1                 sec.-C.sub.5 H.sub.11                                    --     2.9   A.sub.1                 n-C.sub.6 H.sub.13 --     2.10  A.sub.1                 n-C.sub.7 H.sub.15 --     2.11  A.sub.1                 sec.-C.sub.7 H.sub.15                                    --     2.12  A.sub.1                 1-Methylvinyl      --     2.13  A.sub.1                 2-Methylvinyl      --     2.14  A.sub.1                 Allyl              --     2.15  A.sub.1                 2-Methylallyl      --     2.16  A.sub.1                 2-Ethylallyl       --     2.17  A.sub.1                 1-Methylallyl      --     2.18  A.sub.1                 1-Ethylallyl       --     2.19  A.sub.1                 1-Methyl-2-butenyl --     2.20  A.sub.1                 1-Ethyl-2-butenyl  --     2.21  A.sub.1                 1-Isopropyl-2-butenyl                                    --     2.22  A.sub.1                 1-n-Butyl-2-butenyl                                    --     2.23  A.sub.1                 1-Methyl-2-pentenyl                                    --     2.24  A.sub.1                 1,4-Dimethyl-2-pentenyl                                    --     2.25  A.sub.1                 Propargyl          --     2.26  A.sub.1                 2-Butynyl          --     2.27  A.sub.1                 3-Butynyl          --     2.28  A.sub.1                 Ethoxy             --     2.29  A.sub.1                 Propoxy            --     2.30  A.sub.1                 1-Methylethoxy     --     2.31  A.sub.1                 n-Butoxy           --     2.32  A.sub.1                 1-Methylpropoxy    --   46-84     2.33  A.sub.1                 2-Methylpropoxy    --     2.34  A.sub.1                 1,1-Dimethylethoxy --     2.35  A.sub.1                 n-Pentyloxy        --     2.36  A.sub.1                 n-Hexyloxy         --     2.37  A.sub.1                 2-Ethylhexyloxy    --     2.38  A.sub.1                 2-Propenyloxy      --     2.39  A.sub.1                 2-Butenyloxy       --   62-66     2.40  A.sub.1                 2-Methyl-2-propenyloxy                                    --   oil     2.41  A.sub.1                 2-Pentenyloxy      --     2.42  A.sub.1                 3-Pentenyloxy      --     2.43  A.sub.1                 3-chloro-2-propenyloxy                                    --     2.44  A.sub.1                 2,3-Dichloro-2-propenyloxy                                    --     2.45  A.sub.1                 2,3,3-Trichloro-propenyloxy                                    --     2.46  A.sub.1                 2-Propynyloxy      --     2.47  A.sub.1                 2-Butynyl-oxy      --     2.48  A.sub.1                 3-Butynyl-oxy      --     2.49  A.sub.1                 1-Methyl-2-propynyloxy                                    --     2.50  A.sub.1                 Cyclopropyl        --     2.51  A.sub.1                 Cyclobutyl         --     2.52  A.sub.1                 Cyclopentyl        --   112-113     2.53  A.sub.1                 Cyclohexyl         --   120-121     2.54  A.sub.1                 2-Cyclopentenyl    --   128-129     2.55  A.sub.1                 1-Cyclopentenyl    --     2.56  A.sub.1                 2-Cyclohexenyl     --   95-96     2.57  A.sub.1                 1-Cyclohexenyl     --     2.58  A.sub.1                 Cyclopentyloxy     --     2.59  A.sub.1                 Cyclohexyloxy      --     2.60  A.sub.1                 2-Cyclopentenyloxy --     2.61  A.sub.1                 2-Cyclohexenyloxy  --   oil     2.62  A.sub.2                 i-C.sub.3 H.sub.7  CH.sub.2                                          99-101     2.63  A.sub.2                 n-C.sub.3 H.sub.7  CH.sub.2     2.64  A.sub.2                 n-C.sub.4 H.sub.9  CH.sub.2     2.65  A.sub.2                 sec.-C.sub.4 H.sub.9                                    CH.sub.2                                         81-82     2.66  A.sub.2                 i-C.sub.4 H.sub.9  CH.sub.2                                         81-83     2.67  A.sub.2                 tert.-C.sub.4 H.sub.9                                    CH.sub.2     2.68  A.sub.2                 n-C.sub.5 H.sub.11 CH.sub.2     2.69  A.sub.2                 sec.-C.sub.5 H.sub.11                                    CH.sub.2     2.70  A.sub.2                 n-C.sub.6 H.sub.13 CH.sub.2     2.71  A.sub.2                 n-C.sub.7 H.sub.15 CH.sub.2     2.72  A.sub.2                 sec.-C.sub.7 H.sub.15                                    CH.sub.2     2.73  A.sub.2                 1-Methylvinyl      CH.sub.2     2.74  A.sub.2                 2-Methylvinyl      CH.sub.2     2.75  A.sub.2                 Allyl              CH.sub.2     2.76  A.sub.2                 2-Methylallyl      CH.sub.2     2.77  A.sub.2                 2-Ethylallyl       CH.sub.2     2.78  A.sub.2                 1-Methylallyl      CH.sub.2     2.79  A.sub.2                 1-Ethylallyl       CH.sub.2     2.80  A.sub.2                 1-Methyl-2-butenyl CH.sub.2     2.81  A.sub.2                 1-Ethyl-2-butenyl  CH.sub.2     2.82  A.sub.2                 1-Isopropyl-2-butenyl                                    CH.sub.2     2.83  A.sub.2                 1-n-Butyl-2-butenyl                                    CH.sub.2     2.84  A.sub.2                 1-Methyl-2-pentenyl                                    CH.sub.2     2.85  A.sub.2                 1,4-Dimethyl-2-pentenyl                                    CH.sub.2     2.86  A.sub.2                 Propargyl          CH.sub.2     2.87  A.sub.2                 2-Butynyl          CH.sub.2     2.88  A.sub.2                 3-Butynyl          CH.sub.2     2.89  A.sub.2                 Ethoxy             CH.sub.2     2.90  A.sub.2                 Propoxy            CH.sub.2     2.91  A.sub.2                 1-Methylethoxy     CH.sub.2     2.92  A.sub.2                 n-Butoxy           CH.sub.2     2.93  A.sub.2                 1-Methylpropoxy    CH.sub.2     2.94  A.sub.2                 2-Methylpropoxy    CH.sub.2     2.95  A.sub.2                 1,1-Dimethylethoxy CH.sub.2     2.96  A.sub.2                 n-Pentyloxy        CH.sub.2     2.97  A.sub.2                 n-Hexyloxy         CH.sub.2     2.98  A.sub.2                 2-Ethylhexyloxy    CH.sub.2     2.99  A.sub.2                 2-Propenyloxy      CH.sub.2     2.100 A.sub.2                 2-Butentyloxy      CH.sub.2     2.101 A.sub.2                 1-Methyl-2-propenyloxy                                    CH.sub.2                                         67-69     2.102 A.sub.2                 2-Pentenyloxy      CH.sub.2     2.103 A.sub.2                 3-Pentenyloxy      CH.sub.2     2.104 A.sub.2                 3-chloro-2-propenyloxy                                    CH.sub.2     2.105 A.sub.2                 2,3-Dichloro-2-propenyloxy                                    CH.sub.2     2.106 A.sub.2                 2,3,3-Trichloro-Propenyloxy                                    CH.sub.2     2.107 A.sub.2                 2-Propynyloxy      CH.sub.2     2.108 A.sub.2                 2-Butynyl-oxy      CH.sub.2     2.109 A.sub.2                 3-Butynyl-oxy      CH.sub.2     2.110 A.sub.2                 1-Methyl-2-propynyloxy                                    CH.sub.2     2.111 A.sub.2                 Cyclopropyl        CH.sub.2     2.112 A.sub.2                 Cyclobutyl         CH.sub.2     2.113 A.sub.2                 Cyclopentyl        CH.sub.2                                         109-111     2.114 A.sub.2                 Cyclohexyl         CH.sub.2                                         118-123     2.115 A.sub.2                 2-Cyclopentenyl    CH.sub.2                                         87-89     2.116 A.sub.2                 1-Cyclopentenyl    CH.sub.2     2.117 A.sub.2                 2-Cyclohexenyl     CH.sub.2                                         85-87     2.118 A.sub.2                 1-Cyclohexenyl     CH.sub.2     2.119 A.sub.2                 Cyclopentyloxy     CH.sub.2                                         60-91     2.120 A.sub.2                 Cyclohexyloxy      CH.sub.2     2.121 A.sub.2                 2-Cyclopentenyloxy CH.sub.2     2.122 A.sub.2                 2-Cyclohexenyloxy  CH.sub.2                                         oil     2.123 A.sub.2                 i-C.sub.3 H.sub.7  S     2.124 A.sub.2                 n-C.sub.3 H.sub.7  S     2.125 A.sub.2                 n-C.sub.4 H.sub.9  S     2.126 A.sub.2                 sec.-C.sub.4 H.sub.9                                    S    oil     2.127 A.sub.2                 i-C.sub.4 H.sub.9  S    oil     2.128 A.sub.2                 tert.-C.sub.4 H.sub.9                                    S     2.129 A.sub.2                 n-C.sub.5 H.sub.11 S     2.130 A.sub.2                 sec.-C.sub.5 H.sub.11                                    S     2.131 A.sub.2                 n-C.sub.6 H.sub.13 S     2.132 A.sub.2                 n-C.sub.7 H.sub.15 S     2.133 A.sub.2                 sec.-C.sub.7 H.sub.15                                    S     2.134 A.sub.2                 1-Methylvinyl      S     2.135 A.sub.2                 2-Methylvinyl      S     2.136 A.sub.2                 Allyl              S     2.137 A.sub.2                 2-Methylallyl      S     2.138 A.sub.2                 2-Ethylallyl       S     2.139 A.sub.2                 1-Methylallyl      S     2.140 A.sub.2                 1-Ethylallyl       S     2.141 A.sub.2                 1-Methyl-2-butenyl S     2.142 A.sub.2                 1-Ethyl-2-butenyl  S     2.143 A.sub.2                 1-Isopropyl-2-butenyl                                    S     2.144 A.sub.2                 1-n-Butyl-2-butenyl                                    S     2.145 A.sub.2                 1-Methyl-2-pentenyl                                    S     2.146 A.sub.2                 1,4-Dimethyl-2-pentenyl                                    S     2.147 A.sub.2                 Propargyl          S     2.148 A.sub.2                 2-Butynyl          S     2.149 A.sub.2                 3-Butynyl          S     2.150 A.sub.2                 Ethoxy             S     2.151 A.sub.2                 Propoxy            S     2.152 A.sub.2                 1-Methylethoxy     S     2.153 A.sub.2                 n-Butoxy           S     2.154 A.sub.2                 1-Methylpropoxy    S    oil     2.155 A.sub.2                 2-Methylpropoxy    S     2.156 A.sub.2                 1,1-Dimethylethoxy S     2.157 A.sub.2                 n-Pentyloxy        S     2.158 A.sub.2                 n-Hexyloxy         S     2.159 A.sub.2                 2-Ethylhexyloxy    S     2.160 A.sub.2                 2-Propenyloxy      S     2.161 A.sub.2                 2-Butentyloxy      S     2.162 A.sub.2                 1-Methyl-2-propenyloxy                                    S    65-67     2.163 A.sub.2                 2-Pentenyloxy      S     2.164 A.sub.2                 3-Pentenyloxy      S     2.165 A.sub.2                 3-chloro-2-propenyloxy                                    S     2.166 A.sub.2                 2,3-Dichloro-2-propenyloxy                                    S     2.167 A.sub.2                 2,3,3-Trichloro-propenyloxy                                    S     2.168 A.sub.2                 2-Propynyloxy      S     2.169 A.sub.2                 2-Butynyl-oxy      S     2.170 A.sub.2                 3-Butynyl-oxy      S     2.171 A.sub.2                 1-Methyl-2-propynyloxy                                    S     2.172 A.sub.2                 Cyclopropyl        S     2.173 A.sub.2                 Cyclobutyl         S     2.174 A.sub.2                 Cyclopentyl        S    62-64     2.175 A.sub.2                 Cyclohexyl         S    120-122     2.176 A.sub.2                 2-Cyclopentenyl    S    76-78     2.177 A.sub.2                 1-Cyclopentenyl    S     2.178 A.sub.2                 2-Cyclohexenyl     S    70-72     2.179 A.sub.2                 1-Cyclohexenyl     S     2.180 A.sub.2                 Cyclopentyloxy     S    88-90     2.181 A.sub.2                 Cyclohexyloxy      S     2.182 A.sub.2                 2-Cyclopentenyloxy S     2.183 A.sub.2                 2-Cyclohexenyloxy  S    oil     2.184 A.sub.1                 1-Ethylpropoxy     --   65-66     2.185 A.sub.1                 3-Methyl-2-butenyloxy                                    --   oil     2.186 A.sub.2                 1-Ethylpropoxy     CH.sub.2                                         oil     2.187 A.sub.2                 1-Ethylpropoxy     S    oil     ______________________________________

MANUFACTURING EXAMPLES Example 5

At 0° C., 3.1 g of 2-methylbenzoic chloride is dripped into a solution of 3.0 g of sec-butyl-aniline and 2.0 g of triethylamine in 30 ml of tetrahydrofuran, and the mixture is stirred for 2 hours at 0° C. After dilution with 500 ml of water, extraction with ethyl acetate and evaporation of the solvent, there is isolated 2-methylbenzoic acid-2-sec-butylanilide; m.p. 89°-99° C. (Compound No. 2.4).

Example 6

At 0° C., 2.5 g thionyl chloride is dripped into a solution of 3.0 g of 2-methyl-5,6-dihydropyran-3-carboxylic acid. After the mixture has been stirred for 1 hour, 2.8 g of 2-isopropylaniline is added and the whole is stirred for 12 hours at room temperature (20° C.). The pyridine is evaporated off, 50 ml of water is stirred in, the pH is adjusted to 3 with dilute hydrochloric acid, and extraction is carried out with ethyl acetate. The solvent is evaporated, the residue is mixed with diisopropyl ether, and there is isolated 3.3 g of 2-methyl-5,6-dihydropyran-3-carboxylic acid-2-isopropylanilide; m.p.: 99°-101° C. (Compound No. 2.62).

The invention further relates to the use of 2-aminobiphenyl derivatives of the general formula II ##STR10## where the substituents have the following meanings: ##STR11## X methylene, sulfur, sulfinyl, sulfonyl (SO₂), R¹ methyl, trifluoromethyl, chlorine, bromine, iodine,

R² trifluoromethyl, chlorine,

R³ hydrogen or methyl

R⁴ methyl, trifluoromethyl, chlorine

R⁵ hydrogen, methyl, chlorine

R⁶ methyl, trifluoromethyl

R⁷ methyl, chlorine

R⁸ C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, halogen

for combating Botrytis.

The compounds of the formula III are obtained for instance by reacting a correspondingly substituted carboxylic halide of the formula 4 ##STR12## Hal denoting chlorine or bromine, with an ortho-substituted aniline of the formula 5 in the presence of a base. The carboxylic acids and their halides of the formula 4 are known. Some of the anilines of the formula 5 are known or can be prepared by known processes (Tetrahedron Letters, Vol. 28 p. 5093 (1987); THL Vol 295463 (1988)).

                                      TABLE 3     __________________________________________________________________________     No.        A R.sup.1             R.sup.2               R.sup.3                 R.sup.4                    R.sup.5                       R.sup.6                          R.sup.7                            R.sup.8                                 X  Phys. data [°C.]     __________________________________________________________________________     3.1        A.sub.1          CH.sub.3             --               --                 -- -- -- --                            2-F  --     3.2        A.sub.1          CH.sub.3             --               --                 -- -- -- --                            4-F  --     3.3        A.sub.1          CF.sub.3             --               --                 -- -- -- --                            2-F  --     3.4        A.sub.1          CF.sub.3             --               --                 -- -- -- --                            4-F  --     3.5        A.sub.2          -- Cl               --                 -- -- -- --                            2-F  --     3.6        A.sub.2          -- Cl               --                 -- -- -- --                            2-CH.sub.3                                 -- 71-73     3.7        A.sub.2          -- Cl               --                 -- -- -- --                            2-Cl --     3.8        A.sub.2          -- Cl               --                 -- -- -- --                            2-OCH.sub.3                                 --     3.9        A.sub.2          -- Cl               --                 -- -- -- --                            3-F  --     3.10        A.sub.2          -- Cl               --                 -- -- -- --                            3-Cl -- 95-98     3.11        A.sub.2          -- Cl               --                 -- -- -- --                            3-CH.sub.3                                 --     3.12        A.sub.2          -- Cl               --                 -- -- -- --                            3-OCH.sub.3                                 --     3.13        A.sub.2          -- Cl               --                 -- -- -- --                            3-OiC.sub.3 H.sub.7                                 --     3.14        A.sub.2          -- Cl               --                 -- -- -- --                            3-Br --     3.15        A.sub.2          -- Cl               --                 -- -- -- --                            4-F  -- 156-157     3.16        A.sub.2          -- Cl               --                 -- -- -- --                            4-CH.sub.3                                 --     3.18        A.sub.2          -- Cl               --                 -- -- -- --                            4-OCH.sub.3                                 --     3.19        A.sub.2          -- Cl               --                 -- -- -- --                            4-SCH.sub.3                                 --     3.20        A.sub.3          -- --               --                 -- -- -- --                            2-F  CH.sub.2     3.21        A.sub.3          -- --               --                 -- -- -- --                            3-F  CH.sub.2     3.22        A.sub.3          -- --               --                 -- -- -- --                            4-F  CH.sub.2     3.23        A.sub.3          -- --               --                 -- -- -- --                            3-Cl CH.sub.2     3.24        A.sub.3          -- --               --                 -- -- -- --                            3-CH.sub.3                                 CH.sub.2     3.25        A.sub.3          -- --               --                 -- -- -- --                            2-F  S     3.26        A.sub.3          -- --               --                 -- -- -- --                            3-F  S     3.27        A.sub.3          -- --               --                 -- -- -- --                            4-F  S     3.28        A.sub.3          -- --               --                 -- -- -- --                            3-Cl S     3.29        A.sub.3          -- --               --                 -- -- -- --                            3-CH.sub.3                                 S     3.30        A.sub.3          -- --               --                 -- -- -- --                            2-F  SO.sub.2     3.31        A.sub.3          -- --               --                 -- -- -- --                            3-F  SO.sub.2     3.32        A.sub.3          -- --               --                 -- -- -- --                            4-F  SO.sub.2     3.33        A.sub.3          -- --               --                 -- -- -- --                            3-Cl SO.sub.2     3.34        A.sub.3          -- --               --                 -- -- -- --                            3-CH.sub.3                                 SO.sub.2     3.35        A.sub.5          -- --               --                 CF.sub.3                    CH.sub.3                       -- --                            2-F  --     3.36        A.sub.5          -- --               --                 CF.sub.3                    CH.sub.3                       -- --                            3-F  --     3.37        A.sub.5          -- --               --                 CF.sub.3                    CH.sub.3                       -- --                            4-F  --     3.38        A.sub.7          -- --               --                 -- -- CH.sub.3                          Cl                            2-F  --     3.39        A.sub.7          -- --               --                 -- -- CH.sub.3                          Cl                            3-F  --     3.40        A.sub.7          -- --               --                 -- -- CH.sub.3                          Cl                            4-F  --     3.41        A.sub.7          -- --               --                 -- -- CF.sub.3                          Cl                            2-F  --     3.42        A.sub.7          -- --               --                 -- -- CF.sub.3                          Cl                            4-F  --     __________________________________________________________________________

The invention further relates to the use of 2-aminobiphenyl derivatives of the general formula IV ##STR13## where the substituents have the following meanings: ##STR14## X methylene, sulfinyl, sulfonyl (SO₂), R¹ methyl, trifluoromethyl, chlorine, bromine, iodine,

R² trifluoromethyl, chlorine

R³ hydrogen or methyl

R⁴ methyl, trifluoromethyl, chlorine

R⁵ hydrogen, methyl, chlorine

R⁶ methyl, trifluoromethyl

R⁷ methyl, chlorine,

for combating Botrytis.

The compounds of the formula IV are obtained for example by reacting a corresponding aromatic or heterocyclic acid halide 4 with 2-aminobiphenyl 6 in the presence of a base. ##STR15## Hal is chlorine or bromine.

The acids of the formula A-CO₂ H and their halides II are known.

                  TABLE 4     ______________________________________      ##STR16##                                                       Phys.     No.  A     R.sup.1                       R.sup.2                           R.sup.3                                R.sup.4                                     R.sup.5                                          R.sup.6                                              R.sup.7                                                  X    data [°C.]     ______________________________________     4.1  A.sub.1                CH.sub.3                       --  --   --   --   --  --  --   87-88     4.2  A.sub.1                Br     --  --   --   --   --  --  --   113-115     4.3  A.sub.2                --     Cl  --   --   --   --  --  --   151-152     4.4  A.sub.3                --     --  --   --   --   --  --  CH.sub.2                                                       76-77     4.5  A.sub.4                --     --  CH.sub.3                                --   --   --  --  --   104-106     4.6  A.sub.5                --     --  --   CH.sub.3                                     CH.sub.3                                          --  --  --   136-137     ______________________________________

                                      TABLE 5     __________________________________________________________________________     No.        A R.sup.1             R.sup.2                R.sup.3                   R.sup.4                      R.sup.5                         R.sup.6                            R.sup.7                               X  Phys. data [°C.]     __________________________________________________________________________     5.1        A.sub.1          CF.sub.3             -- -- -- -- -- -- -- 138-139     5.2        A.sub.1          J  -- -- -- -- -- -- -- 129-132     5.3        A.sub.2          -- CF.sub.3                -- -- -- -- -- --     5.4        A.sub.3          -- -- -- -- -- -- -- SO.sub.     5.5        A.sub.3          -- -- -- -- -- -- -- SO.sub.2     5.6        A.sub.5          -- -- -- CF.sub.3                      CH.sub.3                         -- -- -- 116-118     5.7        A.sub.6          -- -- -- CH.sub.3                      CH.sub.3                         -- -- --     5.8        A.sub.6          -- -- -- Cl Cl -- -- --     5.9        A.sub.7          -- -- -- -- -- CH.sub.3                            Cl -- 108-109     5.10        A.sub.7          -- -- -- -- -- CF.sub.3                            Cl --     5.11        A.sub.7          -- -- -- -- -- CH.sub.3                            CH.sub.3                               --     5.11        A.sub.1          Cl -- -- -- -- --    -- 100-103     __________________________________________________________________________

The invention further relates to the use of carboxyanilide derivatives of the general formula V ##STR17## where the substituents have the following meanings: ##STR18## n 1 or 2; R¹ trifluoromethyl, chlorine, bromine, iodine,

R² hydrogen or methyl

R³ methyl, trifluoromethyl, chlorine

R⁴ hydrogen, methyl, chlorine,

R⁵ methyl, trifluoromethyl

R⁶ methyl, chlorine

R⁷ unsubstituted or halogen-substituted C₃ -C₁₂ -alkyl, unsubstituted or halogen-substituted C₃ -C₁₂ -alkenyl, C₃ -C₆ -alkynyl, unsubstituted or halogen-substituted C₂ -C₁₂ -alkoxy, unsubstituted or halogen-substituted C₃ -C₁₂ -alkenyloxy, C₃ -C₁₂ -alkynyloxy, unsubstituted or C₁ -C₄ -alkyl-substituted C₃ -C₆ -cycloalkyl, unsubstituted or C₁ -C₄ -alkyl-substituted C₄ -C₆ -cycloalkenyl, unsubstituted or C₁ -C₄ -alkyl-substituted C₅ -C₆ -cycloalkyloxy, unsubstituted or C₁ -C₄ -alkyl-substituted C₅ -C₆ -cycloalkenyloxy

for combating Botrytis.

                  TABLE 6     ______________________________________     Compounds of the formula I where A is A.sub.1      ##STR19##                                     Phys. data     No.  R.sup.1  R.sup.7           mp [°C.]     ______________________________________     6.1  CF.sub.3 i-C.sub.3 H.sub.7 160-162     6.2  CF.sub.3 n-C.sub.3 H.sub.7 151-152     6.3  CF.sub.3 n-C.sub.4 H.sub.9     6.4  CF.sub.3 sec.-C.sub.4 H.sub.9                                     83-84     6.5  CF.sub.3 i-C.sub.4 H.sub.9 133-135     6.6  CF.sub.3 tert.-C.sub.4 H.sub.9     6.7  CF.sub.3 n-C.sub.5 H.sub.11     6.8  CF.sub.3 sec.-C.sub.5 H.sub.11     6.9  CF.sub.3 n-C.sub.6 H.sub.13     6.10 CF.sub.3 n-C.sub.7 H.sub.15     6.11 CF.sub.3 sec.-C.sub.7 H.sub.15     6.12 CF.sub.3 1-Methylvinyl     6.13 CF.sub.3 2-Methylvinyl     6.14 CF.sub.3 Allyl     6.15 CF.sub.3 2-Methylallyl     6.16 CF.sub.3 2-Ethylallyl     6.17 CF.sub.3 1-Methylallyl     6.18 CF.sub.3 1-Ethylallyl     6.19 CF.sub.3 1-Methyl-2-butenyl     6.20 CF.sub.3 1-Ethyl-2-butenyl     6.21 CF.sub.3 1-Isopropyl-2-butenyl     6.22 CF.sub.3 1-n-Butyl-2-butenyl     6.23 CF.sub.3 1-Methyl-2-pentenyl     6.24 CF.sub.3 1,4-Dimethyl-2-pentenyl     6.25 CF.sub.3 Propargyl     6.26 CF.sub.3 2-butynyl     6.27 CF.sub.3 3-butynyl     6.28 CF.sub.3 Ethoxy     6.29 CF.sub.3 Propoxy     6.30 CF.sub.3 1-Methylethoxy     6.31 CF.sub.3 n-Butoxy     6.32 CF.sub.3 1-Methylpropoxy     6.33 CF.sub.3 2-Methylpropoxy     6.34 CF.sub.3 1,1-Dimethylethoxy     6.35 CF.sub.3 n-Pentyloxy     6.36 CF.sub.3 n-Hexyloxy     6.37 CF.sub.3 2-Ethylhexyloxy     6.38 CF.sub.3 2-Propenyloxy     6.39 CF.sub.3 2-Butenyloxy     6.40 CF.sub.3 2-Methyl-2-propenyloxy     6.41 CF.sub.3 2-Pentenyloxy     6.42 CF.sub.3 3-Pentenyloxy     6.43 CF.sub.3 3-chloro-2-propenyloxy     6.44 CF.sub.3 2,3-Dichloro-2-propenyloxy     6.45 CF.sub.3 2,3,3-Trichloro-propenyloxy     6.46 CF.sub.3 2-propynyloxy     6.47 CF.sub.3 2-butynyl-oxy     6.48 CF.sub.3 3-butynyl-oxy     6.49 CF.sub.3 1-Methyl-2-propynyloxy     6.50 CF.sub.3 Cyclopropyl     6.51 CF.sub.3 Cyclobutyl     6.52 CF.sub.3 Cyclopentyl       150-152     6.53 CF.sub.3 Cyclohexyl        130-132     6.54 CF.sub.3 2-Cyclopentenyl   160-161     6.55 CF.sub.3 1-Cyclopentenyl     6.56 CF.sub.3 2-Cyclohexenyl    103-105     6.57 CF.sub.3 1-Cyclohexenyl     6.58 CF.sub.3 Cyclopentyloxy     6.59 CF.sub.3 Cyclohexyloxy     6.60 CF.sub.3 2-Cyclopentenyloxy     6.61 CF.sub.3 2-Cyclohexenyloxy     ______________________________________

                  TABLE 7     ______________________________________     Compounds of the formula V where A is A.sub.1      ##STR20##                                      Phys. data     No.    R.sup.1 R.sup.7           mp [°C.]     ______________________________________     7.1    Cl      i-C.sub.3 H.sub.7 125-127     7.2    Cl      n-C.sub.3 H.sub.7 108-110     7.3    Cl      n-C.sub.4 H.sub.9     7.4    Cl      sec.-C.sub.4 H.sub.9                                      73-74     7.5    Cl      i-C.sub.4 H.sub.9 90-92     7.6    Cl      tert.-C.sub.4 H.sub.9     7.7    Cl      n-C.sub.5 H.sub.11     7.8    Cl      sec.-C.sub.5 H.sub.11     7.9    Cl      n-C.sub.6 H.sub.13     7.10   Cl      n-C.sub.7 H.sub.15     7.11   Cl      sec.-C.sub.7 H.sub.15     7.12   Cl      1-Methylvinyl     7.13   Cl      2-Methylvinyl     7.14   Cl      Allyl     7.15   Cl      2-Methylallyl     7.16   Cl      2-Ethylallyl     7.17   Cl      1-Methylallyl     7.18   Cl      1-Ethylallyl     7.19   Cl      1-Methyl-2-butenyl     7.20   Cl      1-Ethyl-2-butenyl     7.21   Cl      1-Isopropyl-2-butenyl     7.22   Cl      1-n-Butyl-2-butenyl     7.23   Cl      1-Methyl-2-pentenyl     7.24   Cl      1,4-Dimethyl-2-pentenyl     7.25   Cl      Propargyl     7.26   Cl      2-butynyl     7.27   Cl      3-butynyl     7.28   Cl      Ethoxy     7.29   Cl      Propoxy     7.30   Cl      1-Methylethoxy     7.31   Cl      n-Butoxy     7.32   Cl      1-Methylpropoxy     7.33   Cl      2-Methylpropoxy     7.34   Cl      1,1-Dimethylethoxy     7.35   Cl      n-Pentyloxy     7.36   Cl      n-Hexyloxy     7.37   Cl      2-Ethylhexyloxy     7.38   Cl      2-Propenyloxy     7.39   Cl      2-Butentyloxy     7.40   Cl      2-Methyl-2-propenyloxy     7.41   Cl      2-Pentenyloxy     7.42   Cl      3-Pentenyloxy     7.43   Cl      3-chloro-2-propenyloxy     7.44   Cl      2,3-Dichloro-2-propenyloxy     7.45   Cl      2,3,3-Trichloro-propenyloxy     7.46   Cl      2-propynyloxy     7.47   Cl      2-butynyl-oxy     7.48   Cl      3-butynyl-oxy     7.49   Cl      1-Methyl-2-propynyloxy     7.50   Cl      Cyclopropyl     7.51   Cl      Cyclobutyl     7.52   Cl      Cyclopentyl       110-111     7.53   Cl      Cyclohexyl        141-142     7.54   Cl      2-Cyclopentenyl   110-112     7.55   Cl      1-Cyclopentenyl     7.56   Cl      2-Cyclohexenyl    84-86     7.57   Cl      1-Cyclohexenyl     7.58   Cl      Cyclopentyloxy     7.59   Cl      Cyclohexyloxy     7.60   Cl      2-Cyclopentenyloxy     7.61   Cl      2-Cyclohexenyloxy     ______________________________________

                  TABLE 8     ______________________________________     Compounds of the formula V where A is A.sub.2      ##STR21##                                       Phys. data     No.  n        R.sup.7             mp [°C.]     ______________________________________     8.1  2        i-C.sub.3 H.sub.7     8.2  2        n-C.sub.3 H.sub.7     8.3  2        n-C.sub.4 H.sub.9     8.4  2        sec.-C.sub.4 H.sub.9                                       96-98     8.5  2        i-C.sub.4 H.sub.9   85-86     8.6  2        tert.-C.sub.4 H.sub.9     8.7  2        n-C.sub.5 H.sub.11     8.8  2        sec.-C.sub.5 H.sub.11     8.9  2        n-C.sub.6 H.sub.13     8.10 2        n-C.sub.7 H.sub.15     8.11 2        sec.-C.sub.7 H.sub.15     8.12 2        1-Methylvinyl     8.13 2        2-Methylvinyl     8.14 2        Allyl     8.15 2        2-Methylallyl     8.16 2        2-Ethylallyl     8.17 2        1-Methylallyl     8.18 2        1-Ethylallyl     8.19 2        1-Methyl-2-butenyl     8.20 2        1-Ethyl-2-butenyl     8.21 2        1-Isopropyl-2-butenyl     8.22 2        1-n-Butyl-2-butenyl     8.23 2        1-Methyl-2-pentenyl     8.24 2        1,4-Dimethyl-2-pentenyl     8.25 2        Propargyl     8.26 2        2-butynyl     8.27 2        3-butynyl     8.28 2        Ethoxy     8.29 2        Propoxy     8.30 2        1-Methylethoxy     8.31 2        n-Butoxy     8.32 2        1-Methylpropoxy     100-102     8.33 2        2-Methylpropoxy     8.34 2        1,1-Dimethylethoxy     8.35 2        n-Pentyloxy     8.36 2        n-Hexyloxy     8.37 2        2-Ethylhexyloxy     8.38 2        2-Propenyloxy     8.39 2        2-Butenyloxy     8.40 2        2-Methyl-2-propenyloxy     8.41 2        2-Pentenyloxy     8.42 2        3-Pentenyloxy     8.43 2        3-chloro-2-propenyloxy     8.44 2        2,3-Dichloro-2-propenyloxy     8.45 2        2,3,3-Trichloro-propenyloxy     8.46 2        2-propynyloxy     8.47 2        2-butynyl-oxy     8.48 2        3-butynyl-oxy     8.49 2        1-Methyl-2-propynyloxy     8.50 2        Cyclopropyl     8.51 2        Cyclobutyl     8.52 2        Cyclopentyl         128-130     8.53 2        Cyclohexyl          134-135     8.54 2        2-Cyclopentenyl     8.55 2        1-Cyclopentenyl     8.56 2        2-Cyclohexenyl     8.57 2        1-Cyclohexenyl     8.58 2        Cyclopentyloxy     8.59 2        Cyclohexyloxy     8.60 2        2-Cyclopentenyloxy     8.61 2        2-Cyclohexenyloxy     8.62 1        i-C.sub.3 H.sub.7     8.63 1        n-C.sub.3 H.sub.7     8.64 1        n-C.sub.4 H.sub.9     8.65 1        sec.-C.sub.4 H.sub.9                                       oil     8.66 1        i-C.sub.4 H.sub.9   oil     8.67 1        tert.-C.sub.4 H.sub.9     8.68 1        n-C.sub.5 H.sub.11     8.69 1        sec.-C.sub.5 H.sub.11     8.70 1        n-C.sub.6 H.sub.13     8.71 1        n-C.sub.7 H.sub.15     8.72 1        sec.-C.sub.7 H.sub.15     8.73 1        Ethoxy     8.74 1        Propoxy     8.75 1        1-Methylethoxy     8.76 1        n-Butoxy     8.77 1        1-Methylpropoxy     8.78 1        2-Methylpropoxy     8.79 1        1,1-Dimethylethoxy     8.80 1        n-Pentyloxy     8.81 1        n-Hexyloxy     8.82 1        Cyclopentyl     ______________________________________

                  TABLE 9     ______________________________________     Compounds of the formula V where A is A.sub.4      ##STR22##                                         Phys. data     No.   R.sup.3                  R.sup.4                         R.sup.7         mp [°C.]     ______________________________________     9.1   CF.sub.3                  CH.sub.3                         i-C.sub.3 H.sub.7                                         115-116     9.2   CF.sub.3                  CH.sub.3                         n-C.sub.3 H.sub.7                                         114-116     9.3   CF.sub.3                  CH.sub.3                         n-C.sub.4 H.sub.9     9.4   CF.sub.3                  CH.sub.3                         sec.-C.sub.4 H.sub.9                                         73-75     9.5   CF.sub.3                  CH.sub.3                         i-C.sub.4 H.sub.9                                         100-102     9.6   CF.sub.3                  CH.sub.3                         tert.-C.sub.4 H.sub.9     9.7   CF.sub.3                  CH.sub.3                         n-C.sub.5 H.sub.11     9.8   CF.sub.3                  CH.sub.3                         sec.-C.sub.5 H.sub.11     9.9   CF.sub.3                  CH.sub.3                         n-C.sub.6 H.sub.13     9.10  CF.sub.3                  CH.sub.3                         n-C.sub.7 H.sub.15     9.11  CF.sub.3                  CH.sub.3                         sec.-C.sub.7 H.sub.15     9.12  CF.sub.3                  CH.sub.3                         1-Methylvinyl     9.13  CF.sub.3                  CH.sub.3                         2-Methylvinyl     9.14  CF.sub.3                  CH.sub.3                         Allyl     9.15  CF.sub.3                  CH.sub.3                         2-Methylallyl     9.16  CF.sub.3                  CH.sub.3                         2-Ethylallyl     9.17  CF.sub.3                  CH.sub.3                         1-Methylallyl     9.18  CF.sub.3                  CH.sub.3                         1-Ethylallyl     9.19  CF.sub.3                  CH.sub.3                         1-Methyl-2-butenyl     9.20  CF.sub.3                  CH.sub.3                         1-Ethyl-2-butenyl     9.21  CF.sub.3                  CH.sub.3                         1-Isopropyl-2-butenyl     9.22  CF.sub.3                  CH.sub.3                         1-n-Butyl-2-butenyl     9.23  CF.sub.3                  CH.sub.3                         1-Methyl-2-pentenyl     9.24  CF.sub.3                  CH.sub.3                         1,4-Dimethyl-2-pentenyl     9.25  CF.sub.3                  CH.sub.3                         Propargyl     9.26  CF.sub.3                  CH.sub.3                         2-butynyl     9.27  CF.sub.3                  CH.sub.3                         3-butynyl     9.28  CF.sub.3                  CH.sub.3                         Ethoxy     9.29  CF.sub.3                  CH.sub.3                         Propoxy     9.30  CF.sub.3                  CH.sub.3                         1-Methylethoxy     9.31  CF.sub.3                  CH.sub.3                         n-Butoxy     9.32  CF.sub.3                  CH.sub.3                         1-Methylpropoxy     9.33  CF.sub.3                  CH.sub.3                         2-Methylpropoxy     9.34  CF.sub.3                  CH.sub.3                         1,1-Dimethylethoxy     9.35  CF.sub.3                  CH.sub.3                         n-Pentyloxy     9.36  CF.sub.3                  CH.sub.3                         n-Hexyloxy     9.37  CF.sub.3                  CH.sub.3                         2-Ethylhexyloxy     9.38  CF.sub.3                  CH.sub.3                         2-Propenyloxy     9.39  CF.sub.3                  CH.sub.3                         2-Butentyloxy     9.40  CF.sub.3                  CH.sub.3                         2-Methyl-2-propenyloxy     9.41  CF.sub.3                  CH.sub.3                         2-Pentenyloxy     9.42  CF.sub.3                  CH.sub.3                         3-Pentenyloxy     9.43  CF.sub.3                  CH.sub.3                         3-chloro-2-propenyloxy     9.44  CF.sub.3                  CH.sub.3                         2,3-Dichloro-2-propenyloxy     9.45  CF.sub.3                  CH.sub.3                         2,3,3-Trichloro-propenyloxy     9.46  CF.sub.3                  CH.sub.3                         2-propynyloxy     9.47  CF.sub.3                  CH.sub.3                         2-butynyl-oxy     9.48  CF.sub.3                  CH.sub.3                         3-butynyl-oxy     9.49  CF.sub.3                  CH.sub.3                         1-Methyl-2-propynyloxy     9.50  CF.sub.3                  CH.sub.3                         Cyclopropyl     9.51  CF.sub.3                  CH.sub.3                         Cyclobutyl     9.52  CF.sub.3                  CH.sub.3                         Cyclopentyl     114-118     9.53  CF.sub.3                  CH.sub.3                         Cyclohexyl      100-104     9.54  CF.sub.3                  CH.sub.3                         2-Cyclopentenyl 116-120     9.55  CF.sub.3                  CH.sub.3                         1-Cyclopentenyl     9.56  CF.sub.3                  CH.sub.3                         2-Cyclohexenyl  96-98     9.57  CF.sub.3                  CH.sub.3                         1-Cyclohexenyl     9.58  CF.sub.3                  CH.sub.3                         Cyclopentyloxy     9.59  CF.sub.3                  CH.sub.3                         Cyclohexyloxy     9.60  CF.sub.3                  CH.sub.3                         2-Cyclopentenyloxy     9.61  CF.sub.3                  CH.sub.3                         2-Cyclohexenyloxy     9.62  CH.sub.3                  CH.sub.3                         i-C.sub.3 H.sub.7     9.63  CH.sub.3                  CH.sub.3                         n-C.sub.3 H.sub.7     9.64  CH.sub.3                  CH.sub.3                         n-C.sub.4 H.sub.9     9.65  CH.sub.3                  CH.sub.3                         sec.-C.sub.4 H.sub.9                                         136     9.66  CH.sub.3                  CH.sub.3                         i-C.sub.4 H.sub.9                                         96-97     9.67  CH.sub.3                  CH.sub.3                         tert.-C.sub.4 H.sub.9     9.68  CH.sub.3                  CH.sub.3                         n-C.sub.5 H.sub.11     9.69  CH.sub.3                  CH.sub.3                         sec.-C.sub.5 H.sub.11     9.70  CH.sub.3                  CH.sub.3                         n-C.sub.6 H.sub.13     9.71  CH.sub.3                  CH.sub.3                         n-C.sub.7 H.sub.15     9.72  CH.sub.3                  CH.sub.3                         sec.-C.sub.7 H.sub.15     9.73  CH.sub.3                  CH.sub.3                         Ethoxy     9.74  CH.sub.3                  CH.sub.3                         Propoxy     9.75  CH.sub.3                  CH.sub.3                         1-Methylethoxy     9.76  CH.sub.3                  CH.sub.3                         n-Butoxy     9.77  CH.sub.3                  CH.sub.3                         1-Methylpropoxy     9.78  CH.sub.3                  CH.sub.3                         2-Methylpropoxy     9.79  CH.sub.3                  CH.sub.3                         1,1-Dimethylethoxy     9.80  CH.sub.3                  CH.sub.3                         n-Pentyloxy     9.81  CH.sub.3                  CH.sub.3                         n-Hexyloxy     9.82  CH.sub.3                  CH.sub.3                         Cyclopentyl     128-130     9.83  CH.sub.3                  CH.sub.3                         Cyclopentenyl   128-129     9.84  CH.sub.3                  CH.sub.3                         Cyclohexyl      128-129     9.85  CH.sub.3                  CH.sub.3                         1-Ethyl-propoxy 45-47     9.86  CH.sub.3                  CH.sub.3                         Cyclopentyloxy  97-99     9.87  CH.sub.3                  CH.sub.3                         2-Cyclohexenyloxy                                         87-89     9.88  CH.sub.3                  CH.sub.3                         2-Methyl-2-propenyloxy                                         103-105     ______________________________________

                  TABLE 10     ______________________________________     Compounds of the formula V where A is A.sub.6      ##STR23##                                         Phys. data     No.   R.sup.5                  R.sup.6                         R.sup.7         mp [°C.]     ______________________________________     10.1  CH.sub.3                  Cl     i-C.sub.3 H.sub.7                                         108-110     10.2  CH.sub.3                  Cl     n-C.sub.3 H.sub.7                                         129-130     10.3  CH.sub.3                  Cl     n-C.sub.4 H.sub.9     10.4  CH.sub.3                  Cl     sec.-C.sub.4 H.sub.9                                         71-73     10.5  CH.sub.3                  Cl     i-C.sub.4 H.sub.9                                         119-120     10.6  CH.sub.3                  Cl     tert.-C.sub.4 H.sub.9     10.7  CH.sub.3                  Cl     n-C.sub.5 H.sub.11     10.8  CH.sub.3                  Cl     sec.-C.sub.5 H.sub.11     10.9  CH.sub.3                  Cl     n-C.sub.6 H.sub.13     10.10 CH.sub.3                  Cl     n-C.sub.7 H.sub.15     10.11 CH.sub.3                  Cl     sec.-C.sub.7 H.sub.15     10.12 CH.sub.3                  Cl     1-Methylvinyl     10.13 CH.sub.3                  Cl     2-Methylvinyl     10.14 CH.sub.3                  Cl     Allyl     10.15 CH.sub.3                  Cl     2-Methylallyl     10.16 CH.sub.3                  Cl     2-Ethylallyl     10.17 CH.sub.3                  Cl     1-Methylallyl     10.18 CH.sub.3                  Cl     1-Ethylallyl     10.19 CH.sub.3                  Cl     1-Methyl-2-butenyl     10.20 CH.sub.3                  Cl     1-Ethyl-2-butenyl     10.21 CH.sub.3                  Cl     1-Isopropyl-2-butenyl     10.22 CH.sub.3                  Cl     1-n-Butyl-2-butenyl     10.23 CH.sub.3                  Cl     1-Methyl-2-pentenyl     10.24 CH.sub.3                  Cl     1,4-Dimethyl-2-pentenyl     10.25 CH.sub.3                  Cl     Propargyl     10.26 CH.sub.3                  Cl     2-butynyl     10.27 CH.sub.3                  Cl     3-butynyl     10.28 CH.sub.3                  Cl     Ethoxy     10.29 CH.sub.3                  Cl     Propoxy     10.30 CH.sub.3                  Cl     1-Methylethoxy     10.31 CH.sub.3                  Cl     n-Butoxy     10.32 CH.sub.3                  Cl     1-Methylpropoxy     10.33 CH.sub.3                  Cl     2-Methylpropoxy     10.34 CH.sub.3                  Cl     1,1-Dimethylethoxy     10.35 CH.sub.3                  Cl     n-Pentyloxy     10.36 CH.sub.3                  Cl     n-Hexyloxy     10.37 CH.sub.3                  Cl     2-Ethylhexyloxy     10.38 CH.sub.3                  Cl     2-Propenyloxy     10.39 CH.sub.3                  Cl     2-Butentyloxy     10.40 CH.sub.3                  Cl     2-Methyl-2-propenyloxy     10.41 CH.sub.3                  Cl     2-Pentenyloxy     10.42 CH.sub.3                  Cl     3-Pentenyloxy     10.43 CH.sub.3                  Cl     3-chloro-2-propenyloxy     10.44 CH.sub.3                  Cl     2,3-Dichloro-2-propenyloxy     10.45 CH.sub.3                  Cl     2,3,3-Trichloro-propenyloxy     10.46 CH.sub.3                  Cl     2-propynyloxy     10.47 CH.sub.3                  Cl     2-butynyl-oxy     10.48 CH.sub.3                  Cl     3-butynyl-oxy     10.49 CH.sub.3                  Cl     1-Methyl-2-propynyloxy     10.50 CH.sub.3                  Cl     Cyclopropyl     10.51 CH.sub.3                  Cl     Cyclobutyl     10.52 CH.sub.3                  Cl     Cyclopentyl     122-123     10.53 CH.sub.3                  Cl     Cyclohexyl      143-144     10.54 CH.sub.3                  Cl     2-Cyclopentenyl 123-125     10.55 CH.sub.3                  Cl     1-Cyclopentenyl     10.56 CH.sub.3                  Cl     2-Cyclohexenyl  114-116     10.57 CH.sub.3                  Cl     1-Cyclohexenyl     10.58 CH.sub.3                  Cl     Cyclopentyloxy     10.59 CH.sub.3                  Cl     Cyclohexyloxy     10.60 CH.sub.3                  Cl     2-Cyclopentenyloxy     10.61 CH.sub.3                  Cl     2-Cyclohexenyloxy     10.62 CF.sub.3                  Cl     i-C.sub.3 H.sub.7     10.63 CF.sub.3                  Cl     n-C.sub.3 H.sub.7     10.64 CF.sub.3                  Cl     n-C.sub.4 H.sub.9     10.65 CF.sub.3                  Cl     sec.-C.sub.4 H.sub.9                                         108-110     10.66 CF.sub.3                  Cl     i-C.sub.4 H.sub.9                                         122-124     10.67 CF.sub.3                  Cl     tert.-C.sub.4 H.sub.9     10.68 CF.sub.3                  Cl     n-C.sub.5 H.sub.11     10.69 CF.sub.3                  Cl     sec.-C.sub.5 H.sub.11     10.70 CF.sub.3                  Cl     n-C.sub.6 H.sub.13     10.71 CF.sub.3                  Cl     n-C.sub.7 H.sub.15     10.72 CF.sub.3                  Cl     sec.-C.sub.7 H.sub.15     10.73 CF.sub.3                  Cl     Ethoxy     10.74 CF.sub.3                  Cl     Propoxy     10.75 CF.sub.3                  Cl     1-Methylethoxy     10.76 CF.sub.3                  Cl     n-Butoxy     10.77 CF.sub.3                  Cl     1-Methylpropoxy     10.78 CF.sub.3                  Cl     2-Methylpropoxy     10.79 CF.sub.3                  Cl     1,1-Dimethylethoxy     10.80 CF.sub.3                  Cl     n-Pentyloxy     10.81 CF.sub.3                  Cl     n-Hexyloxy     10.82 CF.sub.3                  Cl     Cyclopentyl     113-115     10.83 CF.sub.3                  Cl     Cyclopentenyl   132-133     ______________________________________

                  TABLE 11     ______________________________________     Compounds of the formula V where A is A.sub.7      ##STR24##                                        Phys. data     No.    R.sup.2 R.sup.6 R.sup.7     mp [°C]     ______________________________________     11.1   H       CH.sub.3                            i-C.sub.3 H.sub.7     11.2   H       CH.sub.3                            n-C.sub.3 H.sub.7     11.3   H       CH.sub.3                            n-C.sub.4 H.sub.9     11.4   H       CH.sub.3                            sec.-C.sub.4 H.sub.9                                        oil     11.5   H       CH.sub.3                            i-C.sub.4 H.sub.9                                        oil     11.6   H       CH.sub.3                            tert.-C.sub.4 H.sub.9     11.7   H       CH.sub.3                            n-C.sub.5 H.sub.11     11.8   H       CH.sub.3                            sec.-C.sub.5 H.sub.11     11.9   H       CH.sub.3                            n-C.sub.6 H.sub.13     11.10  H       CH.sub.3                            n-C.sub.7 H.sub.15     11.11  H       CH.sub.3                            sec.-C.sub.7 H.sub.15     11.12  H       CH.sub.3                            Ethoxy     11.13  H       CH.sub.3                            Propoxy     11.14  H       CH.sub.3                            1-Methylethoxy     11.15  H       CH.sub.3                            n-Butoxy     11.16  H       CH.sub.3                            1-Methylpropoxy     11.17  H       CH.sub.3                            2-Methylpropoxy     11.18  H       CH.sub.3                            1,1-Dimethylethoxy     11.19  H       CH.sub.3                            n-Pentyloxy     11.20  H       CH.sub.3                            n-Hexyloxy     11.21  H       CH.sub.3                            Cyclopentyl     11.22  H       CH.sub.3                            Cyclopentenyl     ______________________________________

                  TABLE 12     ______________________________________     Compounds of the formula V where A is A.sub.3      ##STR25##                                    Phys. data     No.    R.sup.2 R.sup.7         mp [°C.]     ______________________________________     12.1   H       i-C.sub.3 H.sub.7                                    147-148     12.2   H       n-C.sub.3 H.sub.7     12.3   H       n-C.sub.4 H.sub.9     12.4   H       sec.-C.sub.4 H.sub.9                                    109-110     12.5   H       i-C.sub.4 H.sub.9                                    114-115     12.6   H       tert.-C.sub.4 H.sub.9     12.7   H       n-C.sub.5 H.sub.11     12.8   H       sec.-C.sub.5 H.sub.11     12.9   H       n-C.sub.6 H.sub.13     12.10  H       n-C.sub.7 H.sub.15     12.11  H       sec.-C.sub.7 H.sub.15     12.12  H       Ethoxy     12.13  H       Propoxy     12.14  H       1-Methylethoxy     12.15  H       n-Butoxy     12.16  H       1-Methylpropoxy     12.17  H       2-Methylpropoxy     12.18  H       1,1-Dimethylethoxy     12.19  H       n-Pentyloxy     12.20  H       n-Hexyloxy     12.21  H       Cyclopentyl     97-98     12.22  H       Cyclohexyl      125-127     12.23  H       2-Cyclopentenyl 98-99     12.24  H       1-Cyclopentenyl     12.25  H       2-Cyclohexenyl  82-84     12.26  H       1-Cyclohexenyl     12.27  H       Cyclopentyloxy  73-75     12.28  H       Cyclohexyloxy     12.29  H       2-Cyclopentenyloxy     12.30  CH.sub.3                    i-C.sub.3 H.sub.7     12.31  CH.sub.3                    n-C.sub.3 H.sub.7     12.32  CH.sub.3                    n-C.sub.4 H.sub.9     12.33  CH.sub.3                    sec.-C.sub.4 H.sub.9                                    80-82     12.34  CH.sub.3                    i-C.sub.4 H.sub.9                                    114-116     12.35  CH.sub.3                    tert.-C.sub.4 H.sub.9     12.36  CH.sub.3                    n-C.sub.5 H.sub.11     12.37  CH.sub.3                    sec.-C.sub.5 H.sub.11     12.38  CH.sub.3                    n-C.sub.6 H.sub.13     12.39  CH.sub.3                    n-C.sub.7 H.sub.15     12.40  CH.sub.3                    sec.-C.sub.7 H.sub.15     12.41  CH.sub.3                    Ethoxy     12.42  CH.sub.3                    Propoxy     12.43  CH.sub.3                    1-Methylethoxy     12.44  CH.sub.3                    n-Butoxy     12.45  CH.sub.3                    1-Methylpropoxy     12.46  CH.sub.3                    2-Methylpropoxy     12.47  CH.sub.3                    1,1-Dimethylethoxy     12.48  CH.sub.3                    n-Pentyloxy     12.49  CH.sub.3                    n-Hexyloxy     12.50  CH.sub.3                    Cyclopentyl     12.51  H       2-Methyl-2-propenyloxy                                    40-41     12.52  H       1-Ethyl-propoxy oil     12.53  H       2-Cyclohexenyloxy                                    51-53     ______________________________________

MANUFACTURING EXAMPLES Example 7

At 0° C., 2.3 g of 2-methyl-4-trifluoromethyl-thiazole-5-carboxylic chloride is dripped into a solution of 1.4 g of 2-n-propylaniline and 1.1 g of triethylamine in 15 ml of tetrahydrofuran, and the mixture is stirred for 12 hours at 20° C.

After dilution with 300 ml of water, extraction with methyl-tert.-butyl ether (12×70 ml), evaporation of the solvent and mixture of the residue with a small amount of n-pentane, there is isolated 2.8 g of 2-methyl-4-trifluromethyl-thiazole-5-carboxylic acid-2-n-propyl-anilide; m.p.: 114°-116° C. (Table 9, No. 2).

Example 8

At 0° C., 3.8 g of 1,3-dimethyl-5-chloroopyrazole-4-carboxylic chloride is dripped into a solution of 2.7 g of 2-isopropylamine and 2.2 g of triethylamine in 40 ml of dichloromethane, and the mixture is stirred for 2 hours at 0° C.

After washing with 50 ml of water, evaporation of the solvent and recrystallization from cyclohexane there is isolated 3.3 g of 1,3-dimethyl-5-chloropyrazole-4-carboxylic acid-2-isopropylanilide; m.p. 108°-110° C. (Table 10, No. 1).

                  TABLE 13     ______________________________________     Compounds of the formula V where A is A.sub.1      ##STR26##                                      Phys. data     No.     R.sup.1                    R.sup.7           mp [°C.]     ______________________________________     13.1    Br     i-C.sub.3 H.sub.7     13.2    Br     n-C.sub.3 H.sub.7     13.3    Br     n-C.sub.4 H.sub.9     13.4    Br     sec.-C.sub.4 H.sub.9                                      74-75     13.5    Br     i-C.sub.4 H.sub.9 110-112     13.6    Br     tert.-C.sub.4 H.sub.9     13.7    Br     n-C.sub.5 H.sub.11     13.8    Br     sec.-C.sub.5 H.sub.11     13.9    Br     n-C.sub.6 H.sub.13     13.10   Br     n-C.sub.7 H.sub.15     13.11   Br     sec.-C.sub.7 H.sub.15     13.12   Br     1-Methylvinyl     13.13   Br     2-Methylvinyl     13.14   Br     Allyl     13.15   Br     2-Methylallyl     13.16   Br     2-Ethylallyl     13.17   Br     1-Methylallyl     13.18   Br     1-Ethylallyl     13.19   Br     1-Methyl-2-butenyl     13.20   Br     1-Ethyl-2-butenyl     13.21   Br     1-Isopropyl-2-butenyl     13.22   Br     1-n-Butyl-2-butenyl     13.23   Br     1-Methyl-2-pentenyl     13.24   Br     1,4-Dimethyl-2-pentenyl     13.25   Br     Propargyl     13.26   Br     2-butynyl     13.27   Br     3-butynyl     13.28   Br     Ethoxy     13.29   Br     Propoxy     13.30   Br     1-Methylethoxy     13.31   Br     n-Butoxy     13.32   Br     1-Methylpropoxy     13.33   Br     2-Methylpropoxy     13.34   Br     1,1-Dimethylethoxy     13.35   Br     n-Pentyloxy     13.36   Br     n-Hexyloxy     13.37   Br     2-Ethylhexyloxy     13.38   Br     2-Propenyloxy     13.39   Br     2-Butentyloxy     13.40   Br     2-Methyl-2-propenyloxy     13.41   Br     2-Pentenyloxy     13.42   Br     3-Pentenyloxy     13.43   Br     3-chloro-2-propenyloxy     13.44   Br     2,3-Dichloro-2-propenyloxy     13.45   Br     2,3,3-Trichloro-propenyloxy     13.46   Br     2-propynyloxy     13.47   Br     2-butynyl-oxy     13.48   Br     3-butynyl-oxy     13.49   Br     1-Methyl-2-propynyloxy     13.50   Br     Cyclopropyl     13.51   Br     Cyclobutyl     13.52   Br     Cyclopentyl     13.53   Br     Cyclohexyl     13.54   Br     2-Cyclopentenyl     13.55   Br     1-Cyclopentenyl     13.56   Br     2-Cyclohexenyl     13.57   Br     1-Cyclohexenyl     13.58   Br     Cyclopentyloxy     13.59   Br     Cyclohexyloxy     13.60   Br     2-Cyclopentenyloxy     13.61   Br     2-Cyclohexenyloxy     ______________________________________

                  TABLE 14     ______________________________________     Compounds of the formula V where A is A.sub.1      ##STR27##                                      Phys. data     No.     R.sup.1                    R.sup.7           mp [°C.]     ______________________________________     14.1    I      i-C.sub.3 H.sub.7     14.2    I      n-C.sub.3 H.sub.7     14.3    I      n-C.sub.4 H.sub.9     14.4    I      sec.-C.sub.4 H.sub.9                                      97-98     14.5    I      i-C.sub.4 H.sub.9 148-149     14.6    I      tert.-C.sub.4 H.sub.9     14.7    I      n-C.sub.5 H.sub.11     14.8    I      sec.-C.sub.5 H.sub.11     14.9    I      n-C.sub.6 H.sub.13     14.10   I      n-C.sub.7 H.sub.15     14.11   I      sec.-C.sub.7 H.sub.15     14.12   I      1-Methylvinyl     14.13   I      2-Methylvinyl     14.14   I      Allyl     14.15   I      2-Methylallyl     14.16   I      2-Ethylallyl     14.17   I      1-Methylallyl     14.18   I      1-Ethylallyl     14.19   I      1-Methyl-2-butenyl     14.20   I      1-Ethyl-2-butenyl     14.21   I      1-Isopropyl-2-butenyl     14.22   I      1-n-Butyl-2-butenyl     14.23   I      1-Methyl-2-pentenyl     14.24   I      1,4-Dimethyl-2-pentenyl     14.25   I      Propargyl     14.26   I      2-butynyl     14.27   I      3-butynyl     14.28   I      Ethoxy     14.29   I      Propoxy     14.30   I      1-Methylethoxy     14.31   I      n-Butoxy     14.32   I      1-Methylpropoxy     14.33   I      2-Methylpropoxy     14.34   I      1,1-Dimethylethoxy     14.35   I      n-Pentyloxy     14.36   I      n-Hexyloxy     14.37   I      2-Ethylhexyloxy     14.38   I      2-Propenyloxy     14.39   I      2-Butentyloxy     14.40   I      2-Methyl-2-propenyloxy     14.41   I      2-Pentenyloxy     14.42   I      3-Pentenyloxy     14.43   I      3-chloro-2-propenyloxy     14.44   I      2,3-Dichloro-2-propenyloxy     14.45   I      2,3,3-Trichloro-propenyloxy     14.46   I      2-propynyloxy     14.47   I      2-butynyl-oxy     14.48   I      3-butynyl-oxy     14.49   I      1-Methyl-2-propynyloxy     14.50   I      Cyclopropyl     14.51   I      Cyclobutyl     14.52   I      Cyclopentyl     14.53   I      Cyclohexyl     14.54   I      2-Cyclopentenyl     14.55   I      1-Cyclopentenyl     14.56   I      2-Cyclohexenyl     14.57   I      1-Cyclohexenyl     14.58   I      Cyclopentyloxy     14.59   I      Cyclohexyloxy     14.60   I      2-Cyclopentenyloxy     14.61   I      2-Cyclohexenyloxy     ______________________________________

                  TABLE 15     ______________________________________     Compounds of the formula V where A is A.sub.3      ##STR28##                                Phys. data     No.      R.sup.7           mp [°C.]     ______________________________________     15.1     i-C.sub.3 H.sub.7     15.2     n-C.sub.3 H.sub.7     15.3     n-C.sub.4 H.sub.9     15.4     sec.-C.sub.4 H.sub.9                                78-80     15.5     i-C.sub.4 H.sub.9 106-107     15.6     tert.-C.sub.4 H.sub.9     15.7     n-C.sub.5 H.sub.11     15.8     sec.-C.sub.5 H.sub.11     15.9     n-C.sub.6 H.sub.13     15.10    n-C.sub.7 H.sub.15     15.11    sec.-C.sub.7 H.sub.15     15.12    Ethoxy     15.13    Propoxy     15.14    1-Methylethoxy     15.15    n-Butoxy     15.16    1-Methylpropoxy     15.17    2-Methylpropoxy     15.18    1,1-Dimethylethoxy     15.19    n-Pentyloxy     15.20    n-Hexyloxy     15.21    Cyclopentyl     15.22    Cyclohexyl     15.23    2-Cyclopentenyl     15.24    1-Cyclopentenyl     15.25    2-Cyclohexenyl     15.26    1-Cyclohexenyl     15.27    Cyclopentyloxy     15.28    Ethoxy     15.29    Propoxy     15.30    1-Methylethoxy     15.31    n-Butoxy     15.32    1-Methylpropoxy     15.33    2-Methylpropoxy     15.34    1,1-Dimethylethoxy     15.35    n-Pentyloxy     15.36    n-Hexyloxy     15.37    2-Ethylhexyloxy     15.38    2-Propenyloxy     15.39    2-Butentyloxy     15.40    2-Methyl-2-propenyloxy                                oil     15.41    2-Pentenyloxy     15.42    3-Pentenyloxy     15.43    3-chloro-2-propenyloxy     15.44    2,3-Dichloro-2-propenyloxy     15.45    2,3,3-Trichloropropenyloxy     15.46    2-Propynyloxy     15.47    2-Butynyl-oxy     15.48    3-Butynyl-oxy     15.49    1-Methyl-2-propynyloxy     15.50    Cyclopropyl     15.51    Cyclobutyl     15.52    Cyclopentyl     15.53    Cyclohexyl     15.54    2-Cyclopentenyl     15.55    1-Cyclopentenyl     15.56    2-Cyclohexenyl     15.57    1-Cyclohexenyl     15.58    Cyclopentyloxy    oil     15.59    Cyclohexyloxy     15.60    2-Cyclopentenyloxy     15.61    2-Cyclohexenyloxy oil     15.62    1-Ethylpropoxy    oil     ______________________________________

The invention further relates to the following novel compounds.

Nicotinic anilide derivatives of the general formula I ##STR29## where the substituents have the following meanings: R¹ halogen, methyl, trifluoromethyl, methoxy, methylthio, methylsulfinyl, methylsulfonyl,

R² unsubstituted or halogen-substituted C₃ -C₁₂ -alkyl, unsubstituted or halogen-substituted C₃ -C₁₂ -alkenyl, C₃ -C₆ -alkynyl, unsubstituted or halogen-substituted C₂ -C₁₂ -alkoxy, unsubstituted or halogen-substituted C₃ -C₁₂ -alkenyloxy, C₃ -C₁₂ -alkynyloxy, C₃ -C₆ -cycloalkyl, C₄ -C₆ -cycloalkenyl, C₅ -C₆ -cycloalkyloxy, C₅ -C₆ -cycloalkenyloxy, with the proviso that R² is not isopropyl when R¹ is chlorine,

Anilide derivatives of the general formula II ##STR30## where the substituents have the following meanings: ##STR31## X methylene or sulfur R unsubstituted or halogen-substituted C₃ -C₁₂ -alkyl, unsubstituted or halogen-substituted C₃ -C₁₂ -alkenyl, C₃ -C₆ -alkynyl, unsubstituted or halogen-substituted C₂ -C₁₂ -alkoxy, unsubstituted or halogen-substituted C₃ -C₁₂ -alkenyloxy, C₃ -C₁₂ -alkynyloxy, unsubstituted or C₁ -C₄ -alkyl-substituted C₃ -C₆ -cycloalkyl, unsubstituted or C₁ -C₄ -alkyl-substituted C₄ -C₆ -cycloalkenyl, unsubstituted or C₁ -C₄ -alkyl-substituted C₅ -C₆ -cycloalkyloxy, unsubstituted or C₁ -C₄ -alkyl-substituted C₅ -C₆ -cycloalkenyloxy

with the proviso that

A is not A₁ when R is ethoxy, isopropoxy or allyloxy,

A is not A₂, X denoting sulfur, when R is ethoxy, propoxy, n-butoxy, sec.-butoxy or n-pentyloxy,

A is not A₂, X denoting methylene, when R is isopropyl.

2-Aminobiphenyl derivatives of the general formula III, ##STR32## where the substituents have the following meanings: ##STR33## X methylene, sulfur, sulfinyl, sulfonyl (SO₂), R¹ methyl, trifluoromethyl, chlorine, bromine, iodine

R² trifluoromethyl, chlorine

R³ hydrogen or methyl

R⁴ methyl, trifluoromethyl, chlorine

R⁵ hydrogen, methyl, chlorine

R⁶ methyl, trifluoromethyl

R⁷ methyl, chlorine

R⁸ C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, halogen.

Carboxanilide derivatives of the general formula V ##STR34## where the substituents have the following meanings: ##STR35## n 1 or 2 R¹ trifluoromethyl, chlorine, bromine, iodine,

R² hydrogen or methyl

R³ methyl, trifluoromethyl, chlorine

R⁴ hydrogen, methyl, chlorine

R⁵ methyl, trifluoromethyl

R⁶ methyl, chlorine

R⁷ unsubstituted or halogen-substituted C₃ -C₁₂ -alkyl, unsubstituted or halogen-substituted C₃ -C₁₂ -alkenyl, C₃ -C₆ -alkynyl, unsubstituted or halogen-substituted C₂ -C₁₂ -alkoxy, unsubstituted or halogen-substituted C₃ -C₁₂ -alkenyloxy, C₃ -C₁₂ -alkynyloxy, unsubstituted or C₁ -C₄ -alkyl-substituted C₅ -C₆ -cycloalkyl, unsubstituted or C₁ -C₄ -alkyl-substituted C₄ -C₆ -cycloalkenyl, unsubstituted or C₁ -C₄ -alkyl-substituted C₅ -C₆ -cycloalkenyloxy, with the proviso that R⁷ is not 3-methyl-but-2-en-1-yl or 3-methyl- but-3-en-1-yl when R¹ is trifluoromethyl.

The novel compounds are suitable as fungicides.

The fungicidal compounds according to the invention, or agents containing them, may be applied for instance in the form of directly sprayable solutions, powders, suspensions (including high-percentage aqueous, oily or other suspensions), dispersions, emulsions, oil dispersions, pastes, dusts, broadcasting agents, or granules by spraying, atomizing, dusting, broadcasting or watering. The forms of application depend entirely on the purpose for which the agents are being used, but they must ensure as fine a distribution of the active ingredients according to the invention as possible.

Normally, the plants are sprayed or dusted with the active ingredients, or the seeds of the plants are treated with the active ingredients.

The formulations are produced in known manner, for example by extending the active ingredient with solvents and/or carriers, with or without the use of emulsifiers and dispersants; if water is used as solvent, it is also possible to employ other organic solvents as auxiliary solvents. Suitable auxiliaries for this purpose are solvents such as aromatics (e.g., xylene), chlorinated aromatics (e.g., chlorobenzenes), paraffins (e.g., crude oil fractions), alcohols (e.g., methanol, butanol), ketones (e.g., cyclohexanone), amines (e.g., ethanolamine, dimethylformamide), and water; carriers such as ground natural minerals (e.g., kaolins, aluminas, talc and chalk) and ground synthetic minerals (e.g., highly disperse silica and silicates); emulsifiers such as nonionic and anionic emulsifiers (e.g., polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates); and dispersants such as lignin-sulfite waste liquors and methylcellulose.

Examples of surfactants are: alkali metal, alkaline earth metal and ammonium salts of aromatic sulfonic acids, e.g., ligninsulfonic acid, phenolsulfonic acid, naphthalenesulfonic acid and dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl and alkylaryl sulfonates, and alkyl, lauryl ether and fatty alcohol sulfates, and salts of sulfated hexadecanols, heptadecanols, and octadecanols, salts of fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ethers, ethoxylated isooctylphenol, ethoxylated octylphenol and ethoxylated nonylphenol, alkylphenol polyglycol ethers, tributylphenyl polyglycol ethers, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin-sulfite waste liquors and methyl cellulose.

Examples of surfactants are: alkali metal, alkaline earth metal and ammonium salts of aromatic sulfonic acids, e.g., ligninsulfonic acid, phenolsulfonic acid, naphthalenesulfonic acid and dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl and alkylaryl sulfonates, and alkyl, lauryl ether and fatty alcohol sulfates, and salts of sulfated hexadecanols, heptadecanols, and octadecanols, salts of fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ethers, ethoxylated isooctylphenol, ethoxylated octylphenol and ethoxylated nonylphenol, alkylphenol polyglycol ethers, tributylphenyl polyglycol ethers, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin-sulfite waste liquors and methyl cellulose.

Powders, dusts and broadcasting agents may be prepared by mixing or grinding the active ingredients with a solid carrier.

Granules, e.g., coated, impregnated or homogeneous granules, may be prepared by bonding the active ingredients to solid carriers. Examples of solid carriers are mineral earths such as silicic acids, silica gels, silicates, talc, kaolin, attapulgus clay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, and ureas, and vegetable products such as grain meals, bark meal, wood meal, and nutshell meal, cellulosic powders, etc.

Examples of formulations are given below.

I. A solution of 90 parts by weight of compound no. 1.7 and 10 parts by weight of N-methyl-α-pyrrolidone, which is suitable for application in the form of very fine drops.

II. A mixture of 20 parts by weight of compound no. 1.8, 80 parts by weight of xylene, 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide and 1 mole of oleic acid-N-monoethanolamide, 5 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, and 5 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By finely dispersing the mixture in water, an aqueous dispersion is obtained.

III. An aqueous dispersion of 20 parts by weight of compound no. 1.3, 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil.

IV. An aqueous dispersion of 20 parts by weight of compound no. 1.4, 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction having a boiling point between 210° and 280° C., and 10 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil.

V. A hammer-milled mixture of 80 parts by weight of compound no. 1.5, 3 parts by weight of the sodium salt of diisobutylnaphthalene-α-sulfonic acid, 10 parts by weight of the sodium salt of a lignin-sulfonic acid obtained from a sulfite waste liquor, and 7 parts by weight of powdered silica gel. By finely dispersing the mixture in water, a spray liquor is obtained.

VI. An intimate mixture of 3 part by weight of compound no. 1.7 and 97 parts by weight of particulate kaolin. The dust contains 3 wt % of the active ingredient.

VII. An intimate mixture of 30 parts by weight of compound no. 1.8, 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil sprayed onto the surface of this silica gel. This formulation of the active ingredient exhibits good adherence.

VIII. A stable aqueous dispersion of 40 parts by weight of compound no. 1.9, 10 parts by weight of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate, 2 parts by weight of silica gel and 48 parts by weight of water, which dispersion can be further diluted.

IX. A stable oily dispersion of 20 parts by weight of compound no. 1.33, 2 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight of a fatty alcohol polyglycol ether, 20 parts by weight of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate and 68 parts by weight of a paraffinic mineral oil.

The novel compounds are extremely effective on a broad spectrum of phytopathogenic fungi, in particular Botrytis. Some of them have a systemic action and can be used as foliar and soil fungicides.

The fungicidal compounds are of particular interest for controlling a large number of fungi in various crops or their seeds, especially wheat, rye, barley, oats, rice, Indian corn, lawns, cotton, soybeans, coffee, sugar cane, fruit and ornamentals in horticulture and viticulture, and in vegetables such as cucumbers, beans and cucurbits.

The compounds are applied by treating the fungi or the seeds, plants or materials threatened by fungus attack, or the soil with a fungicidally effective amount of the active ingredients.

The agents may be applied before or after infection of the materials, plants or seeds by the fungi.

The novel compounds are particularly useful for controlling the following plant diseases:

Erysiphe graminis in cereals,

Erysiphe cichoracearum and Sphaerotheca fuliginea in cucurbits,

Podosphaera leucotricha in apples,

Uncinula necator in vines,

Venturia inaequalis (scab) in apples,

Helminthosporium species in cereals,

Septoria nodorum in wheat,

Botrytic cinerea (gray mold) in strawberries and grapes,

Cercospora arachidicole in groundnuts,

Pseudocercosporella herpotrichoides in wheat and barley,

Pyricularia oryzae in rice,

Fusarium and Verticillium species in various plants,

Alternaria species in fruit and vegetables.

Use against Botrytis is preferred.

The novel compounds may also be used for protecting materials (timer), e.g., against Paecilomyces variotii.

The fungicidal agents generally contain from 0.1 to 95, and preferably from 0.5 to 90, wt % of active ingredient.

The application rates depend on the type of effect desired, and range from 0.02 to 3 kg of active ingredient per hectare.

When the active ingredients are used for treating seed, rates of 0.001 to 50, and preferably from 0.01 to 10, g per kg of seed are generally sufficient.

In these application forms, the agents according to the invention may also be present together with other active ingredients, for example herbicides, insecticides, growth regulators, and other fungicides, and may furthermore be mixed and applied together with fertilizers. Admixture with other fungicides frequently results in a greater fungicidal action spectrum.

The following list of fungicides with which the novel compounds may be combined is intended to illustrate possible combinations but not to impose any restrictions.

Examples of fungicides which may be combined with the novel compounds are:

sulfur, dithiocarbamates and their derivatives, such as ferric dimethyldithiocarbamate, zinc dimethyldithiocarbamate, zinc ethylenebisdithiocarbamate, manganese ethylenebisdithiocarbamate, manganese zinc ethylenediaminebisdithiocarbamate, tetramethylthiuram disulfides, ammonia complex of zinc N,N'-ethylenebisdithiocarbamate, ammonia complex of zinc N,N'-propylenebisdithiocarbamate, zinc N,N'-propylenebisdithiocarbamate and N,N'-polypropylenebis(thiocarbamyl) disulfide;

nitro derivatives, such as dinitro(1-methylheptyl)-phenyl crotonate, 2-sec-butyl-4,6-dinitrophenyl 3,3-dimethylacrylate, 2-sec-butyl-4,6-dinitrophenyl isopropylcarbonate and diisopropyl 5-nitroisophthalate;

heterocyclic substances, such as 2-heptadecylimidazol-2-yl acetate, 2,4-dichloro-6-(o-chloroanilino)-s-triazine, O,O-diethyl phthalimidophosphonothioate, 5-amino-1-[-bis-(dimethylamino)-phosphinyl]-3-phenyl-1,2,4-triazole, 2,3-dicyano-1,4-dithioanthraquinone, 2-thio-1,3-dithio[4,5-b]quinoxaline, methyl 1-(butylcarbamyl)-2-benzimidazolecarbamate, 2-methoxycarbonylaminobensimidazole, 2-(fur-2-yl)-benzimidazole, 2-(thiazol-4-yl)benzimidazole, N-(1,1,2,2-tetrachloroethylthio)-tetrahydrophthalimide, N-trichloromethylthiotetrahydrophthalimide, N-trichloromethylthiophthalimide,

N-dichlorofluoromethylthio-N',N'-dimethyl-N-phenylsulfuric acid diamide, 5-ethoxy-3-trichloromethyl-1,2,3-thiadiazole, 2-thiocyanatomethylthiobenzothiazole, 1,4-dichloro-2,5-dimethoxybenzene, 4-(2-chlorophenylhydrazono)-3-methyl-5-isoxazolone, 2-thiopyridine 1-oxide, 8-hydroxyquinoline and its copper salt, 2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiyne, 2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiyne 4,4-dioxide, 2-methyl-5,6-dihydro-4H-pyran-3-carboxanilide, 2-methylfuran-3-carboxanilide, 2,5-dimethylfuran-3-carboxanilide, 2,4,5-trimethylfuran-3-carboxanilide, 2,5-dimethyl-N-cylcohexylfuran-3-carboxamide, N-cyclohexyl-N-methoxy-2,5-diethylfuran-3-carboxamide, 2-methylbenzanilide, 2-iodobenzanilide, N-formyl-N-morpholine-2,2,2-trichloroethylacetal, piperazine-1,4-diylbis-(1-(2,2,2-trichloroethyl)-formamide), 1-(3,4-dichloroanilino)-1-formylamino-2,2,2-trichloroethane, 2,6-dimethyl-N-tridecylmorpholine and its salts, 2,6-dimethyl-N-cyclododecylmorpholine and its salts, N[3-(p-tert.-butylphenyl)-2-methylpropyl]-cis-2,6-dimethylmorpholine, N-3-(p-tert.-butylphenyl)-2-methylproply'-piperidine, 1-2-(2,4-dichlorophenyl)-4-ethyl-1,3-dioxolan-2-yl-ethyl'-1H-1,2,4-triazole, 1-[2-(2,4-dichlorophenyl)-4-n-propyl-1,3-dioxolan-2-yl-ethyl]-1H-1,2,4-triazole, N-(n-propyl)-N-(2,4,6-trichlorophenoxyethyl)-N'-imidazolyl-urea, 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-tri-azol-1-yl)-butan-2-one, 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-butan-2-ol, α-(2-chlorophenyl)-α-(4-chlorophenyl)-5-pyrimidinemethanol, 5-butyl-(2-dimethylamino-4-hydroxy-6-methylpyrimidine, bis-(p-chlorophenyl)-3-pyridinemethanol, 1,2-bis-(3-ethoxycarbonyl-2-thioureido)-benzene, 1,2-bis-(3-methoxycarbonyl-2-thioureido)-benzene, and various fungicides, such as dodecylguanidine acetate, 3-[3-(3,5-dimethyl-2-oxycyclohexyl)-2-hydroxyethyl]-glutaramide, hexachlorobenzene, DL-methyl-N-(2,6-dimethylphenyl)-N-fur-2-yl alanate, methyl DL-N-(2,6-dimethylphenyl)-N-(2'-methoxyacetyl)-alanate, N-(2,6-dimethylphenyl)-N-chloroacetyl-DL-2-aminobutyrolactone, methyl DL-N-(2,6-dimethylphenyl)-N-(phenylacetyl)-alanate, 5-methyl-5-vinyl-3-(3,5-dichlorophenyl)-2,4-dioxo-1,3-oxazolidine, 3-[3,5-dichlorophenyl]-5-methyl-5-methoxymethyl-1,3-oxazolidine-2,4-dione, 3-(3,5-dichlorophenyl)-1-isopropylcarbamylhydantoin, N-(3,5-dichlorophenyl)-1,2-dimethylcyclopropane-1,2-dicarboximide, 2-cyano-[N-(ethylaminocarbonyl)-2-methoximino]-acetamide, 1-[2-(2,4-dichlorophenyl)-pentyl]-1H-1,2,4-triazole, 2,4-difluoro-α-(1H-1,2,4-triazol-1-ylmethyl)-benzhydryl alcohol, N-(3-chloro-2,6-dinitro-4-trifluoromethylphenyl)-5-trifluoromethyl-3-chloro-2-aminopyridine, and 1-((bis-(4-fluorophenyl)-methylsilyl)-methyl)-1H-1,2,4-triazole.

USE EXAMPLES

The active ingredients 2-chloronicotic acid-2'-ethylanilide (A)--disclosed in U.S. Pat. No. 4,001,416--and 2-chloronicotic acid-3'-isopropylanilide (B)--disclosed in DE 26 11 601--were used for comparison purposes.

Use Example 1 Action on Botrytis cinerea in Paprika

Slices of green paprika pods were sprayed to runoff with aqueous suspensions containing (dry basis) 80% of active ingredient and 20% of emulsifier. Two hours after the sprayed-on layer had dried, the slices were inoculated with a spore suspension of the fungus Botrytis cinerea, which contained 1.7×10⁶ spores per ml of a 2% strength malt solution. The inoculated slices were then incubated in humid chambers at 18° C. for 4 days. The development of Botrytis on the slices attacked was then assessed visually.

The results show that active ingredients 1.5, 1.7 and 1.8, applied as spray liquors containing 600 ppm of active ingredient, have a better fungicidal action (95%) than prior art comparative compounds A (10%) and B (65%).

Use Example 2 Action on Botrytis cinerea in Paprika

Paprika pods were slit open and the inside surfaces were sprayed to runoff with aqueous active ingredient formulations containing (dry basis) 80% of active ingredient and 20% of emulsifier. After the sprayed-on layer had dried, the pieces were inoculated with an aqueous suspension containing 1.7×10⁶ spores of Botrytis cinerea per ml.

The paprika pieces were then kept for 4 days in climatic cabinets at 20°-22° C. The extent of fungus spread was then assessed visually.

The results show that compounds 2.4, 4.4, 6.4, 7.4, 7.5, 9.1, 9.2, 9.4, 9.5, 10.1, 10.2, 10.4, 10.5, 12.4, 12.6, 2.65 and 2.66, applied as aqueous spray liquors containing 1,000 ppm of active ingredient, have a good fungicidal action (100%). 

We claim:
 1. A method of treating Botrytis infestation comprising applying to a subject in need thereof, an effective amount of an anilide derivative of the formula ##STR36## wherein A is 1-methylpyrazol-4-yl substituted in the 3-position by methyl, chloro or trifluoromethyl and substituted in the 5-position by chloro;R is unsubstituted or halogen-substituted C₃ -C₁₂ -alkyl, unsubstituted or halogen-substituted C₃ -C₁₂ -alkenyl, C₃ -C₆ -alkynyl, unsubstituted or halogen-substituted C₂ -C₁₂ -alkoxy, unsubstituted or halogen-substituted C₃ -C₁₂ -alkenyloxy, C₃ -C₁₂ -alkynyloxy, or phenyl which is unsubstituted or substituted by C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio or halogen; in a suitable carrier.
 2. A method of treating Botrytis infestation comprising applying to a subject in need thereof, an effective amount of a 2-aminobiphenyl derivative of the formula III ##STR37## wherein A is a group of formula ##STR38## R⁶ is methyl or trifluoromethyl; R⁷ is chloro; andR⁸ is C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio or halogen;in a suitable carrier.
 3. A method of treating Botrytis infestation comprising applying to a subject in need thereof, an effective amount of a 2-aminobiphenyl derivative of the formula IV ##STR39## wherein A is a group of formula ##STR40## R⁶ is methyl, or trifluoromethyl; and R⁷ is chloro;in a suitable carrier.
 4. A method of treating Botrytis infestation comprising applying to a subject in need thereof, an effective amount of a carboxanilide derivative of the general formula V ##STR41## wherein A is a group of formula: ##STR42## R⁵ is methyl or trifluoromethyl; R⁶ is chloro; andR⁷ is unsubstituted or halogen-substituted C₃ -C₁₂ -alkyl, unsubstituted or halogen-substituted C₃ -C₁₂ -alkenyl, C₃ -C₆ -alkynyl, unsubstituted or halogen-substituted C₂ -C₁₂ -alkoxy, unsubstituted or halogen-substituted C₃ -C₁₂ -alkenyloxy or C₃ -C₁₂ -alkynyloxy;in a suitable carrier.
 5. A 2-aminobiphenyl derivative of the formula III ##STR43## wherein A is a group of formula ##STR44## R⁶ is methyl or trifluoromethyl; R⁷ is chloro; andR⁸ is C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio or halogen.
 6. A composition useful in the treatment of Botrytis infestation, comprising an effective amount of a compound as claimed in claim 5, in a suitable carrier.
 7. A carboxanilide derivative of the formula V ##STR45## wherein A is a group of formula: ##STR46## R⁵ is methyl or trifluoromethyl; R⁶ is chloro; andR⁷ is unsubstituted or halogen-substituted C₃ -C₁₂ -alkenyloxy or C₃ -C₁₂ -alkynyloxy.
 8. A composition useful in the treatment of Botrytis infestation, comprising an effective amount of a compound as claimed in claim 7, in a suitable carrier. 